[1] He made his debut in the Third Division on 14 December 1991 in a 2–1 defeat at AFC Bournemouth,[3] and played in the Football League Trophy four days later,[4] but after a few months he was allowed to leave for Cobh Ramblers.
[1] After a spell with Dagenham & Redbridge, Cheesewright joined Braintree Town, where he impressed sufficiently to earn a move back to the Football League with Colchester United.
In June 1995 he appeared on loan for Wimbledon in a 4–0 defeat to Bursaspor in a group match of the 1995 UEFA Intertoto Cup, when English clubs were not taking the competition seriously.
[2] He then spent brief periods with Romford,[8] Aldershot Town,[9] and Heybridge Swifts,[10] before attempting a return to the Football League with Barnet, where he signed as goalkeeping cover just before the April 1998 transfer deadline.
[11] Without playing for Barnet, Cheesewright moved on to play for a number of teams in the Hertfordshire and Essex area, including St Albans City,[12] Leyton Pennant,[13] Braintree Town,[14] Heybridge Swifts (again),[15] and finally, in 2000, as an outfield player for Eton Manor in the Essex Senior League.