Robbie Simpson
Robbie Simpson (born 15 March 1985) is an English former professional footballer who played as a centre-forward, later transitioning to management and financial services.[1] During his playing career, spanning from 2003 to 2022, Simpson featured for multiple clubs across England's lower leagues, including Cambridge United, Coventry City, Huddersfield Town, Brentford, Oldham Athletic, Leyton Orient, and Exeter City, accumulating over 200 appearances in League One and League Two.[2] He began his professional journey with Cambridge United in 2006 after time at non-league Cambridge City, and notably experienced loans and permanent moves that took him through all four divisions below the Premier League.[3] Simpson retired as a player in July 2022 while with Chelmsford City in the National League South.[1] In 2020, Simpson took up the managerial role at Chelmsford City, leading the club to a second-place finish in the National League South during the 2023–24 season and achieving several club records, and stepped down from his managerial role at the end of the 2024–25 season, as announced in January 2025.[4] His tenure marked a successful stint in non-league football, blending his playing experience with leadership.[5] Simpson co-founded Life After Professional Sport (LAPS) in 2016, a consultancy supporting athletes in career transitions, and established RS19 Ltd in 2019, where he serves as founder and managing director offering lifestyle financial planning services.[6][7] A graduate of Loughborough University with a degree in sports science and mathematics, Simpson's work now focuses on empowering former sports professionals through financial advisory and career guidance.[8]Early life and education
Early years
Robbie Simpson was born on 15 March 1985 in Poole, Dorset, England.[9][3] His first organized involvement in the sport came in the mid-1990s when, at age nine, he joined the youth academy of Norwich City on schoolboy terms.[10]University studies
Simpson enrolled at Loughborough University in 2004, pursuing a joint honours BSc in Sports Science and Mathematics while continuing his semi-professional football career with Cambridge City.[8][11] The dual degree program combined sports science and mathematical principles, providing a broad perspective applicable to football.[8][12] During his studies, Simpson joined the Loughborough University football team, ultimately leading to a professional contract offer after his second year.[8] Balancing rigorous academic demands with frequent training sessions and matches presented significant challenges, including disrupted sleep from midweek social activities affecting early lectures and the need to commute for semi-professional games.[8][12] In June 2006, Simpson signed his first professional contract with Cambridge United, overlapping with his final year of study; the club supported his completion of the degree, which he earned with a 2:1 honours in July 2007.[8][11] This period marked a pivotal transition, as the academic framework equipped him with quantitative skills for performance analysis that complemented his on-field development.[13]Playing career
Norwich City
Simpson joined Norwich City's academy system at the age of nine, beginning his entry into professional football structures as a promising forward.[10] Over the subsequent years, he progressed through the club's age-group teams, appearing in the Under-15 squad during the 1999/2000 season, where the team faced notable opponents like Manchester United in youth fixtures.[14] By the 2000/01 campaign, Simpson had advanced to the Under-16 side, training alongside emerging talents such as Ian Henderson.[15] His time at the academy concluded in July 2002, when he was released amid increasing competition for forward positions in the youth setup.[16] Following his departure from Norwich, Simpson moved to non-league club Cambridge City to continue his development.[17]Cambridge City
After being released by Norwich City, Robbie Simpson signed with Cambridge City in 2002 at the age of 17, seeking regular first-team opportunities in semi-professional football.[18] He quickly established himself as a key player in the Southern League Premier Division, making his senior debut in October 2002 and becoming a regular starter as a forward.[19] Over five seasons from 2002 to 2006, Simpson made 154 appearances and scored 42 goals for Cambridge City, contributing significantly to the team's attacking play with his pace, positioning, and finishing ability.[19] His goals often came from exploiting spaces behind defenses, providing a tactical outlet in counter-attacks and helping maintain the team's competitiveness in the non-league pyramid. During this period, he balanced his burgeoning football career with university studies in sports science and mathematics at Loughborough University.[8] The 2004–05 season stood out as a breakthrough year, with Simpson featuring prominently in both league and cup competitions. Cambridge City mounted a strong promotion push, finishing in the upper echelons of the Southern League Premier Division table, though they ultimately fell short in the playoffs. In the FA Cup, Simpson contributed to an impressive run that saw the team defeat higher-tier opponents, including Conference North side Leigh RMI in the first round proper, before advancing to the second round where they faced League One's Milton Keynes Dons—entering as a substitute in the 1–0 home defeat.[20] These matches against professional clubs highlighted his potential and composure under pressure.Cambridge United (first spell)
In June 2006, Robbie Simpson signed his first professional contract with Cambridge United on a free transfer from local non-league club Cambridge City, marking his transition to full-time professional football in the Conference National.[21] Despite initial challenges including a knee injury and balancing full-time studies at Loughborough University, he quickly adapted to the demands of the fifth tier.[22] During the 2006–07 season, Simpson made 33 appearances and scored 17 goals across all competitions, with 15 of those strikes coming after the turn of the year as he found his rhythm.[23] His debut goal arrived in a 2–1 defeat to Weymouth on 19 August 2006, heading in a corner from Michael Taylor to briefly reduce the arrears.[24] A prolific run followed, highlighted by a brace in a 3–0 home win over Woking on 27 January 2007—where he was denied a hat-trick by a fine save—and his first career hat-trick in a 4–0 victory at Northwich Victoria on 24 March 2007, which propelled Cambridge into the top half of the table late in the campaign.[25][26] These contributions were instrumental in Cambridge United's survival, as the team finished 17th and avoided relegation to the Conference North.[22] Simpson's form attracted interest from higher divisions, leading to his departure from Cambridge United in July 2007 for a transfer to Championship side Coventry City, with the fee to be settled by an independent tribunal.Coventry City
Simpson joined Coventry City in July 2007 on a two-year contract following a successful trial period with the club.[27] Having impressed manager Iain Dowie with his goalscoring form at Cambridge United in League Two, where he netted 17 goals in 33 appearances the previous season, Simpson earned a move to the Championship side as part of Dowie's squad rebuild.[28] During his two seasons at Coventry, Simpson made 61 appearances and scored 4 goals, predominantly coming off the bench due to stiff competition from established forwards such as Leon Best, Michael Mifsud, and Dele Adebola.[29] His debut proved memorable, scoring after just five minutes in a 3-1 League Cup victory over Notts County in August 2007, though subsequent opportunities were limited by the higher level of competition and his adjustment from non-league and League Two football.[30] Injuries further restricted his playing time, including a ruptured hamstring in November 2007 that sidelined him for around two months, impacting his integration into the first team.[31] Simpson's tenure highlighted the challenges of stepping up to the Championship, where he struggled for consistent starts and managed only three league goals across 28 Championship outings, often deployed in a supporting role rather than as a primary striker.[32] Despite occasional bright moments, such as assisting in key matches, his limited impact reflected the difficulties of adapting to the physical and tactical demands of second-tier football after prolific lower-league spells. In June 2009, with his contract set to expire, Simpson transferred to Huddersfield Town for a reported £300,000 fee.[33]Huddersfield Town
Simpson joined Huddersfield Town on 18 June 2009 from Coventry City for a reported fee of £300,000, signing a three-year contract with the League One club.[34] Over his spell at the club from 2009 to 2012, he made 13 appearances in League One without scoring a goal, frequently remaining on the substitutes' bench behind established forwards such as Alan Lee, Lee Novak, and later Jordan Rhodes.[35] Despite limited first-team opportunities, Simpson contributed positively during training sessions and earned occasional starts in cup competitions, including two appearances in the 2009–10 League Cup where he scored once in a 3–1 first-round victory over Stockport County.[35][36] With his playing time curtailed by injuries and competition for places, Simpson opted for loan moves to Brentford in 2010 and Oldham Athletic in 2011 to secure regular football and rebuild his match sharpness.[37][38]Brentford (loan)
In August 2010, Robbie Simpson joined Brentford on a season-long loan from Huddersfield Town, providing attacking depth to the Bees' squad in League One.[39] The move allowed him to regain match fitness after limited opportunities at his parent club, where his contract situation had limited his playing time.[37] During the 2010–11 season, Simpson made 27 appearances in League One for Brentford, scoring 4 goals and contributing to their push for a playoff position, as the team finished seventh in the table, just one point shy of the top six.[23] His goals included a header in a 2–1 opening-day victory over Cheltenham Town on 10 August 2010, an equalizer in a 1–3 home defeat to Rochdale on 28 August 2010, the winner in a 2–1 triumph against Dagenham & Redbridge on 11 December 2010, and a late header securing a 1–0 away win at Rochdale on 16 April 2011, which helped maintain Brentford's momentum in the promotion race.[40] These strikes exemplified his role as a versatile forward, often operating as a substitute to provide impact from the bench while supporting the starting strikers.[41] Beyond league play, Simpson added 4 goals in cup competitions, including a decisive strike in Brentford's 1–0 Johnstone's Paint Trophy first-round win over Stevenage on 7 September 2010, aiding their progress to the southern section semi-finals. Overall, the loan proved successful in rebuilding his confidence and form, with Simpson later reflecting on fond memories of the club despite a hamstring injury sidelining him for over a month mid-season.[37] He returned to Huddersfield at the end of the campaign in May 2011, having made 36 appearances and scored 8 goals in all competitions for Brentford.[16]Oldham Athletic (loan)
Following a difficult spell at Huddersfield Town, where Simpson found himself isolated from the first-team squad and limited to bench roles, he returned to Oldham Athletic on a short-term loan in early January 2012. The arrangement, completed just days before the FA Cup third-round tie against Liverpool on 6 January, was explicitly with a view to a permanent deal and allowed him to resume training with the Latics during the intervening period after his initial loan expired in December 2011.[38][42] Simpson marked his debut for the second loan spell with a memorable contribution, scoring a stunning 25-yard volley to give Oldham a shock lead against the Premier League side at Anfield; although Liverpool ultimately won 5-1, the goal highlighted his technical ability and composure under pressure.[43] Over the course of the loan, which ran until late January, he featured in a handful of matches across League One and cup competitions, providing positive contributions that impressed manager Paul Dickov.[44] Despite the encouraging start, minor injuries restricted Simpson's opportunities for full integration into the squad during this brief period. Team-mates and coaching staff praised his work ethic and attitude, noting his value in adding depth to the forward line amid a congested fixture schedule.[45] The loan concluded in January 2012 without extension, but it directly facilitated Simpson's permanent transfer to Oldham later that month, enabling him to remain with the club through the end of the season.[46]Oldham Athletic
Following a successful loan spell that familiarized him with the club, Simpson joined Oldham Athletic on a permanent basis on 30 January 2012, signing a contract until the end of the 2011–12 season. He quickly became an integral part of the squad under manager Paul Dickov, contributing to the team's mid-table stability in League One. In June 2012, Simpson extended his stay with a one-year deal, committing to the club through the 2012–13 campaign.[46][47] Over his permanent tenure from January 2012 to May 2013, Simpson made 66 appearances and scored 7 goals across all competitions, primarily in League One, where Oldham secured 17th-place finishes in both seasons to ensure survival. His versatility as a forward allowed him to feature regularly, often starting matches and providing crucial contributions in tight relegation battles. Notable moments included scoring twice in a dramatic 2–1 FA Cup third-round victory over Nottingham Forest in January 2013, helping propel Oldham to the fourth round. Simpson's work rate and reliability earned him fan favorite status at Boundary Park, with supporters appreciating his role in high-profile upsets.[23][48] In April 2013, Simpson was appointed club captain by interim manager Lee Johnson, stepping into a leadership role during a challenging run-in that saw Oldham avoid relegation. He embraced the "midfield general" responsibilities, guiding the team through key fixtures despite injury setbacks that limited his goal output in the second season. At the end of his contract in May 2013, Simpson was released by Oldham as part of a squad overhaul, prompting him to seek new challenges elsewhere to reignite his career.[49][50]Leyton Orient
In November 2013, Robbie Simpson signed for League One club Leyton Orient on an initial two-month contract as a free agent following his release from Oldham Athletic.[51] The move came amid Orient's strong promotion push, as they sat atop the table early in the 2013–14 season, and Simpson was viewed as a potential boost to their attacking options.[52] In January 2014, his deal was extended until the end of the season, reflecting initial promise despite limited early involvement.[53] During the 2013–14 campaign, Simpson made 14 appearances in League One for Orient, starting five matches and accumulating 474 minutes, but he failed to score any goals.[23] His role was primarily as a squad player, often coming off the bench, including in cup competitions where he featured as a substitute in the FA Cup and Johnstone's Paint Trophy.[54] A dip in form and stiff competition from established forwards like Kevin Lisbie and Scott McGleish restricted his opportunities, as Orient maintained a top-three position for much of the season but ultimately finished in sixth place after playoffs.[55] Simpson's stint at Orient proved unfulfilling, marking a transitional low point in his career with minimal impact during the club's promotion aspirations. In May 2014, he was among five players released by the club at the end of his contract, paving the way for a return to Cambridge United.[56][57]Cambridge United (second spell)
Simpson rejoined Cambridge United on 9 June 2014, signing a two-year contract as a free agent following his release from Leyton Orient.[56] The 29-year-old forward returned to the club shortly after their promotion to League Two via the Conference Premier play-offs, leveraging his familiarity from a previous stint between 2006 and 2007.[58] Over the course of his second spell, Simpson made 77 appearances and scored 13 goals in all competitions from 2014 to 2016, serving as an experienced presence in the attack.[35] In the 2014–15 season, he featured in 41 matches, netting 9 goals, including a notable strike in the FA Cup third-round win over Luton Town.[35][59] His contributions helped stabilize the team during their adjustment to full-time League Two football, where he praised the club's enhanced professionalism compared to his earlier time there.[22] The 2015–16 campaign saw Simpson appear 36 times and score 4 goals, providing reliable leadership amid a mid-table finish, though his output reflected his advancing age.[35] He departed the club by mutual consent at the end of his contract on 9 May 2016, after discussions failed to yield a new deal.[60]Exeter City
Simpson joined Exeter City on a free transfer from Cambridge United on 25 May 2016, signing a two-year contract as a 31-year-old forward.[61][16] During his tenure from July 2016 to June 2018, Simpson made 42 appearances across all competitions, scoring 3 goals, primarily in League Two.[16] His goals came in league matches: the opener in a 3–2 away win against Colchester United on 3 September 2016,[62] an equalizer against Cheltenham Town on 2 April 2018 after returning from injury, and the winner in a 1–0 home win over Colchester United on 5 May 2018.[63][64][65] In his debut season (2016-17), Simpson featured regularly as an experienced striker, contributing to Exeter's ninth-place finish in League Two with 26 league appearances and 1 goal, helping secure a play-off spot that ended in semi-final defeat.[66] The following year was disrupted by a broken ankle in February 2017, limiting him to 11 league appearances and 2 goals upon his March 2018 return, as Exeter again finished mid-table in eighth place.[67][66] His physical presence and hold-up play provided squad depth and support in attack, aiding the team's stability during a competitive campaign that saw them reach the League Two play-off final.[68] Simpson was released by Exeter at the end of his contract in June 2018, alongside six other players, as the club reshaped its squad.[69] He subsequently signed a short-term deal with Milton Keynes Dons for a fresh challenge in League Two.[68]Milton Keynes Dons
Robbie Simpson signed a short-term deal with Milton Keynes Dons on 9 July 2018, shortly after his departure from Exeter City, joining the club following their relegation from EFL League One the previous season.[70] At 33 years old, the experienced forward provided depth to the attacking options under manager Paul Tisdale as the team sought an immediate return to the third tier. In November 2018, Tisdale confirmed that Simpson's contract would be extended through to the end of the 2018–19 campaign, allowing him to contribute more substantially to the squad.[71] During the 2018–19 EFL League Two season, Simpson featured in 21 league matches for MK Dons, scoring 2 goals while primarily operating as a substitute or rotational striker.[23] His debut came as a substitute in a 3–2 away win over Cambridge United on 4 August 2018, and he marked his first goal for the club by netting within a minute of entering as a second-half replacement in a 1–1 home draw against Grimsby Town on 21 August. His second league goal arrived in a 3–0 victory over Yeovil Town on 20 October 2018. Simpson's role emphasized physical presence and hold-up play in the forward line, supporting key attackers like Kieran Agard and Chuks Aneke during a campaign where MK Dons amassed 79 points to secure third place and automatic promotion via a 1–0 win over Mansfield Town on the final day.[72] Following promotion, Simpson was released in May 2019 as part of a broader squad restructuring, with 16 players retained and several others departing to refresh the team for League One.[73] This marked the end of his professional career in the English Football League, after which he transitioned to non-league football with Chelmsford City.Chelmsford City
Simpson joined Chelmsford City on 15 August 2019 as a free agent player in the National League South, following his release from Milton Keynes Dons.[74][75] Upon taking over as caretaker manager in January 2020 and securing the role permanently in March 2020, Simpson transitioned into a player-coach position, balancing on-pitch duties with leadership responsibilities.[76] Over the next four seasons, he made 21 appearances and scored 4 goals across all competitions, primarily in the 2019–20 campaign with 15 appearances and all of his goals that season, before his involvement tapered off significantly from 2020–21 onward (4 appearances) and into 2021–22 (2 appearances), with no further outings by 2022–23 as his focus shifted to management.[35] Simpson retired from playing at the end of the 2021–22 season to concentrate fully on his managerial duties.[1]Managerial career
Appointment at Chelmsford City
On 29 January 2020, Chelmsford City parted company with long-serving manager Rod Stringer, prompting the club to appoint Robbie Simpson as interim first-team manager the following day.[77][78] At the time, Simpson was still an active player for the National League South side, having joined the club in 2019, and he agreed to lead the team while continuing his on-pitch duties.[76] Simpson's successful interim stint, which saw the team remain unbeaten in four matches, led to his permanent appointment on 11 March 2020, where he signed a long-term contract to provide stability amid growing uncertainties from the emerging COVID-19 pandemic.[76][79] The timing was particularly challenging, as the National League South season was soon suspended due to the virus, with Simpson expressing surprise that a match against Dartford proceeded on 14 March before the full shutdown.[80] This disruption effectively retained the existing squad without immediate changes, allowing Simpson to focus on foundational planning rather than mid-season overhauls. Influenced by his academic background—a degree in Sports Science and Mathematics from Loughborough University—and coaching qualifications earned during his playing career, including the UEFA B licence, Simpson brought a structured approach to his new role.[11][6] His prior involvement in establishing the club's new academy informed early decisions to prioritize youth integration, emphasizing opportunities for young players to transition into the first team alongside retaining core squad members for continuity in the National League South.[76]Tenure and achievements
Simpson's tenure as Chelmsford City manager began amid the challenges of the COVID-19 pandemic, with his permanent appointment in March 2020 following an interim spell. Over the subsequent seasons, he established a reputation for steady improvement, leading the Clarets to consistent top-half finishes in the National League South and two playoff campaigns by 2024. His leadership emphasized disciplined squad management and fostering team cohesion, contributing to the club's highest league points tally in the 2023–24 season.[4] In the 2020–21 season, curtailed by the pandemic, Simpson guided Chelmsford through a limited fixture schedule, securing four wins in 15 league games for a mid-table position before the campaign was declared null and void. This period tested his ability to adapt to restricted training and matches, laying foundational work for future stability despite the absence of playoffs.[81] Chelmsford's 2023–24 season marked a high point under Simpson, as the team finished second with 84 points, their best-ever league performance. They reached the semi-finals of the playoffs but fell 2–3 after extra time to Braintree Town, ending promotion hopes. Key contributions came from forwards like Michael Cheek, who scored 23 goals, highlighting Simpson's focus on clinical finishing. Simpson received the National League South Manager of the Month award in January 2024 for overseeing three wins in three games, including a 3–1 victory over Hampton & Richmond Borough. His tactical approach prioritized defensive solidity—conceding the fewest goals in the league that season—while promoting controlled, possession-based play to dominate matches.[82][83][84] On a limited budget, Simpson excelled in squad building by integrating young talents and loanees, such as developing prospects from EFL academies into first-team contributors, which enhanced the club's competitiveness without major spending. This strategy underscored his emphasis on player development, turning raw potential into reliable performers aligned with a balanced, attacking ethos when opportunities arose.Retirement from management
On 11 January 2025, Chelmsford City Football Club announced that Robbie Simpson would step down from his role as first-team manager at the conclusion of the 2024–25 National League South season, marking his retirement from management after more than five years in charge.[4] Simpson, who had managed 218 games for the club with a 41% win ratio, expressed that the decision was driven by personal factors unrelated to the team's performance or club direction.[4] During the 2024–25 season, Chelmsford City finished 11th in the National League South table, securing a mid-table position with 62 points from 46 matches, including 16 wins, 14 draws, and 16 losses.[85] The campaign emphasized a transitional phase, with Simpson prioritizing the integration of younger players through the newly launched under-21 team, established in June 2024 as part of the club's development pathway and overseen by first-team staff.[86] This initiative aimed to build long-term sustainability amid the season's challenges, though promotion—a stated goal at the announcement—remained elusive.[4] Simpson cited family priorities as a primary reason for his retirement, noting conflicts between the football calendar and his children's school schedules, as well as a long-standing promise to his wife to reclaim family weekends following his playing retirement six years earlier.[4] He also highlighted growing commitments to his financial planning business, RS19 Ltd, which demanded more time and aligned poorly with the club's evolving needs after five demanding years.[87] While not explicitly attributing burnout, Simpson reflected on the personal toll of the role in a period marked by a family bereavement in April 2025.[88] Simpson's tenure left a lasting legacy at Chelmsford, including advocacy for infrastructure enhancements such as transitioning to full-time operations, with a formal assessment planned post-season to support future growth.[89] He fostered strong fan relations, earning widespread appreciation for creating memorable experiences and maintaining open communication, as evidenced by supporter tributes during his final home game on 21 April 2025.[90] Simpson committed to aiding the transition by assisting in the successor search, ensuring continuity as Angelo Harrop took over on 19 May 2025.[91]Personal life
Family and residence
Robbie Simpson is married to Nicola Simpson, with whom he started a family later in his career following years of professional commitments. The couple welcomed their daughter Rosie around the time of Simpson's move to Chelmsford City in 2019.[92] Simpson's playing career, spanning clubs across England from Huddersfield Town in Yorkshire to Brentford in London and Coventry in the Midlands, involved frequent relocations that tested family stability but were supported by his wife's understanding. By 2019, the family had settled in the Chelmsford area of Essex.[93] Simpson and his family have maintained a private personal life away from the public eye, avoiding any reported scandals or controversies throughout his time in professional football. His 2025 retirement from management was partly motivated by a commitment to prioritize time with his wife and children after years of demanding schedules.[4]Post-playing interests
Following his retirement from playing in 2022, Robbie Simpson channeled his energies into entrepreneurial pursuits aimed at supporting fellow athletes. He co-founded LAPS (Life After Professional Sport) in 2016, a platform dedicated to assisting elite sports professionals in transitioning to post-career opportunities through career guidance, CV preparation, and job placement services.[6] LAPS has partnered with organizations like the Professional Footballers' Association to provide resources for retiring players.[94] Simpson also established RS19 Ltd in 2019, where he serves as founder and managing director, offering lifestyle financial planning tailored to athletes and high-net-worth individuals navigating life after sport.[87] His 2007 degree in Sports Science and Mathematics from Loughborough University informs his advisory role, particularly in areas of financial wellness and long-term planning for sports-related injuries or career shifts.[8] In addition to business endeavors, Simpson has engaged in community initiatives, notably supporting Holly's Fund, a charity established in memory of a family member to aid early years education and special educational needs programs in Essex.[95] He has promoted fundraising events for the cause via social media, emphasizing legacy-building projects like sensory play installations for children.[96] Simpson's retirement from management in 2025 has allowed greater focus on these interests, with interviews indicating aspirations to grow his financial services business while exploring non-football avenues such as broader consulting.[4]Career statistics
Club playing statistics
Robbie Simpson's club playing statistics encompass appearances and goals in league, cup, and playoff competitions across his career from 2002 to 2022, totaling 523 appearances and 103 goals. A significant portion of his early goal-scoring came at Cambridge City, where he netted 33 goals in 118 appearances. The following table aggregates his statistics by club, drawing from verified records; note that some seasons include loans, and post-2019 data reflects limited playing time at Chelmsford City due to increasing managerial responsibilities. Norwich City involvement was at youth level with no senior appearances.[33][29][35]| Club | Seasons | Total Appearances | Total Goals |
|---|---|---|---|
| Norwich City | 2003–2006 | 0 | 0 |
| Cambridge City | 2002–2006 | 118 | 33 |
| Cambridge United (first spell) | 2006–2007 | 33 | 17 |
| Coventry City | 2007–2009 | 71 | 7 |
| Huddersfield Town | 2009–2013 | 16 | 1 |
| Brentford (loan) | 2010–2011 | 36 | 8 |
| Oldham Athletic | 2011–2013 | 60 | 13 |
| Leyton Orient | 2013–2014 | 16 | 0 |
| Cambridge United (second spell) | 2014–2016 | 75 | 13 |
| Exeter City | 2016–2018 | 41 | 3 |
| Milton Keynes Dons | 2018–2019 | 24 | 2 |
| Chelmsford City | 2019–2022 | 31 | 6 |
Managerial record
Simpson managed Chelmsford City from January 2020 until the end of the 2024–25 season, overseeing 216 competitive matches in total, comprising league fixtures, cup ties, and playoff games. His overall record stood at 84 wins, 58 draws, and 74 losses, for a win percentage of 38.9% and an average of 1.44 points per match. This encompassed the primary National League South campaign, along with sporadic appearances in the FA Cup, FA Trophy, and promotion playoffs, where the team reached the semi-finals in 2022–23 (loss to St Albans City, 0–1) and 2023–24 (loss to Braintree Town, 2–3 aggregate).[99] In league play specifically, Simpson's tenure saw gradual improvement, with win percentages rising from low-20s in the early disrupted seasons to over 50% in the playoff-qualifying campaigns of 2022–23 and 2023–24, though the 2024–25 season ended in mid-table consolidation. The partial 2020–21 season was declared null and void, but historical records note the performance for context. Cup results were modest, with 4 wins, 3 draws, and 8 losses across 15 matches (win percentage 26.7%), including early exits in the FA Cup proper.[100]| Season | Competition | Played (P) | Wins (W) | Draws (D) | Losses (L) | Win % | Notes |
|---|---|---|---|---|---|---|---|
| 2019–20 | National League South | 6 | 3 | 2 | 1 | 50.0% | Partial season (Feb–Mar); suspended due to COVID-19; PPG 1.83. |
| 2020–21 | National League South | 16 | 4 | 4 | 8 | 25.0% | Shortened season; declared null and void; PPG 1.00. No cups advanced. |
| 2021–22 | National League South | 40 | 9 | 14 | 17 | 22.5% | Relegation battle avoided (5 pts clear); PPG 1.03. Limited cup involvement (1 win, 2 losses). |
| 2022–23 | National League South | 46 | 23 | 9 | 14 | 50.0% | Playoff qualification; PPG 1.70. Playoffs: 0W, 0D, 1L. FA Cup: 0W, 0D, 1L. |
| 2023–24 | National League South | 46 | 24 | 12 | 10 | 52.2% | Record 84 points; runners-up. Playoffs: 0W, 0D, 1L. FA Trophy: 2W, 1L. |
| 2024–25 | National League South | 46 | 16 | 14 | 16 | 34.8% | Mid-table finish; PPG 1.35. No playoffs; 1 cup win, 1 loss. |
| Total | All Competitions | 216 | 84 | 58 | 74 | 38.9% | Includes 190 league matches (58.3% of total); playoff seasons highlighted for promotion pushes. Home record: 49W, 30D, 29L (53.8% win rate); away: 35W, 28D, 45L (30.4% win rate). Against top-5 opponents: 12W, 8D, 15L (33.3% win rate). |