Career
As a midfielder, he played for India between 1995 and 2001, when he announced his retirement. At the club level, he had a successful career, having had two spells with East Bengal and one with JCT Mills. As a coach, he had a 6-year spell with I-League 2nd Division club Tata Football Academy from 2002 to 2008, and then with Royal Wahingdoh Football Club. He is currently the head coach of Students Union of the Bangalore Super Division.
Chapman began his club career with Sai Centre, Bangalore in the mid-1980s.
He then played for Southern Blues, a Bangalore club, and Tata Football Academy, Jamshedpur, before signing for East Bengal in 1993. He had a fruitful two years at Bengal until signed by JCT Mills in 1995.
After one season with Kochi in 1997-1998, Chapman returned to his former club, East Bengal in 1998. In the Santosh Trophy, Chapman played for Karnataka, Punjab and West Bengal.
2002–2013
Following his retirement from playing, Chapman coached the Tata Football Academy team, then in I-League 2nd Division, from 2002 to 2008.
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.
2013–present
In 2013, he was signed by Bhawanipore Football Club, a Kolkata based club, that plays in the I-League 2nd Division, after having missed qualifying to the first division by a point in the 2013 season.