Background
Cheesewright was born in Romford, Havering.
Cheesewright was born in Romford, Havering.
He played as a goalkeeper. He began his football career as a trainee with Tottenham Hotspur, but was released in 1981 without playing for the first team He joined Southend United, but again failed to appear for the first team
After a spell in non-league football with Kingsbury Town, he signed for Birmingham City, initially on a non-contract basis, in 1991.
He made his debut in the Third Division on 14 December 1991 in a 2–1 defeat at A.F.C. Bournemouth, and played in the Football League Trophy four days later, but after a few months he was allowed to leave for Cobh Ramblers. 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.
The fee, of £10,000, was Braintree"s record transfer fee received, and Cheesewright went on to play 40 league games for Colchester. A stint with Mansion in the Hong Kong First Division League preceded another return to the Football League, this time with Wycombe Wanderers, where he played 18 league games.
He then spent brief periods with Romford, Aldershot Town, and Heybridge Swifts, before attempting a return to the Football League with Barnet, where he signed as goalkeeping cover just before the April 1998 transfer deadline.
Without playing for Barnet, Cheesewright moved on to play for a number of teams in the Hertfordshire and Essex area, including Street Albans City, Leyton Pennant, Braintree Town, Heybridge Swifts (again), and finally, in 2000, as an outfield player for Eton Manor in the Essex Senior League. As of 2008, Cheesewright was married with two children and was working as a wealth planning manager for a major bank.