Chesterfield Chapman signed for
Chesterfield from nearby non-league side
Belper Town in the summer of 2013. He joined
Chester on a one-month loan in February 2014. He made his professional debut on 2 September in the
Football League Trophy match against
Scunthorpe United, after coming off the bench to replace
Tommy Lee in the seventh minute. On 23 September 2014, Chapman joined
Accrington Stanley on a two-month loan deal. On 11 October, he had to be substituted in the closing stages of Accrington Stanley's 2–1 home defeat to
Dagenham & Redbridge following an injury to his left foot. His loan spell was cut short and he returned to Chesterfield on 13 October, having played three games for Accrington. On 14 August 2015, Chapman joined
Bristol Rovers on a one-month loan deal.
Accrington Stanley In summer 2016, Chapman joined
Accrington Stanley on a two-year contract. In an
EFL Cup tie against
Bradford City on 9 August 2016, Chapman came on as a substitute after
Elliot Parish was sent off. The game went to a penalty shootout which Stanley won 11–10 and Chapman took and scored a penalty. Accrington Stanley won the League Two title in 2017–18, with Chapman also winning the
League Two Golden Glove award, having kept 18 clean sheets in 45 league games. At the end of the 2017–18 season, he was offered a new contract by Accrington.
Peterborough United On 15 May 2018, Chapman joined
Peterborough United on a two-year deal to challenge the number 1 Jersey. He was transfer-listed by Peterborough United at the end of the 2018–19 season. On 14 December 2019, Chapman joined
Tranmere Rovers on a one-week emergency loan. On 12 June 2020, Chapman was released by Peterborough, after playing 39 games for the club.
Motherwell On 7 October 2020, Chapman was announced as a new signing by
Scottish Premiership club
Motherwell, with manager
Stephen Robinson describing him as being "experienced cover and competition to
Trevor" (Carson). He was released by the club at the end of the
2020–21 season.
Gillingham On 6 July 2021, Chapman returned to England to join League One side
Gillingham following his release from Motherwell. Chapman was released by the club following relegation to League Two at the end of the
2021–22 season.
Stevenage On 23 May 2022, Chapman signed for League Two side
Stevenage, playing under
Steve Evans for a third time in the career with the manager having signed him at both Peterborough United and Gillingham.
Non-League career In February 2023, Chapman signed for
National League side
Scunthorpe United after finding limited opportunities to play in Steve Evans' Stevenage side. He was released in December 2023 and signed for
Northern Counties East League Division One side
Retford United. Three weeks later, without Retford having played a game in the intervening period, he joined
Boston United of the
National League North. In March 2024, he joined
Handsworth. On 5 June 2024, Chapman joined National League North side
Hereford. He made 19 appearances for
The Bulls before signing for
Southern League Premier Division Central club
Spalding United for an undisclosed fee in January 2025. ==Personal life==