Chapman began his club career with Sai Centre, Bangalore in the mid-1980s. He then played for Southern Blues, a Bangalore club, before joining the Tata Football Academy as a cadet in 1990. He stayed with the club till 1993 after graduating the previous year, before signing for East Bengal. He had a fruitful two years at Bengal until signed by JCT Mills in 1995. In 1993, his first season with Bengal, he scored a hat-trick against the Iraqi club Al-Zawra at the Asian Cup Winners' Cup, a match that Bengal won 6–2. During his spell at JCT Mills, the team won 14 tournaments, with a team that had I. M. Vijayan and Baichung Bhutia, both of whom are regarded as India's all-time greats. After one season with FC Kochi in 1997–98, Chapman returned to his former club East Bengal in 1998. The team won the National Football League under his captaincy in 2001, before he announced his retirement from professional football. In the Santosh Trophy, Chapman played for Karnataka, Punjab and West Bengal.
Coaching career
2002–2013
Following his retirement as a player, Chapman coached the Tata Football Academy team, then in I-League 2nd Division, from 2002 to 2008. He was signed in December 2002 on a one-year contract as an assistant to head coach Ranjan Choudhary and assistant coachVijay Kumar. He quit in 2008, after the team was not allowed to play in the first division by its management even after having qualified. During these years, he had stints with the Indian under-19 team as an assistant coach and with the Jharkhand under-19 team in 2003 and 2005. Following his departure from Tata Football Football Academy, he had a stint with a New Delhi club, Royal Rangers, in 2008. He was then approached by Royal Wahingdoh, a club based in Shillong. He guided the team to three successive Shillong Premier League wins, and the Bordoloi Trophy win in 2011.
2013–2017
In 2013, Chapman was signed by Bhawanipore FC, a Kolkata-based club, that played in the I-League 2nd Division, after they failed to qualify for the first division by a point in the previous season. In 2014, he joined Students Union that competed in the Bangalore Super Division. In 2017, he joined Sudeva Moonlight FC, a club based in Delhi, as an assistant coach. Under him, the club got promoted to the I-League 2nd Division.
2017–present
In December 2017, Chapman was appointed the Technical Director of the Kozhikode-based Quartz International Football Academy.