Dean started his playing career as an apprentice with Watford and was given a contract shortlafter his 18th birthday in November 1986. In February 1988, he went out on loan to Carlisle United, and then Port Vale the following month until the end of the season. After further loan spells at Swansea City and Brentford during the following season, he signed for Brentford in September 1989. After three years at Brentford where he scored 53 goals in 110 League appearances, he signed for Wimbledon for £720,000 where he was a member of the infamous "Crazy Gang" . His prolific goalscoring earmed him a £3½ million move to Bolton Wanderers in October 1997. After a loan move to Coventry City in November 2002, he signed for them before joining Rushden & Diamonds on 27 March 2003 on a non-contract basis until the end of the season.

Dean failed to win a permanent contract at the end of the season, and re-joined Wimbledon (later becoming MK Dons) on 23 May 2003. He went on to join Havant & Waterlooville in a player/coach role, then joined Derby County as assistant to manager Phil Brown. After Brown was sacked in January 2006, Dean then moved to a succession of clubs - Weymouth, Heybridge Swifts, Cambridge United and Newport County. He became player/manager of Redbridge in July 2007, leading them to third place in the Isthmian League Division One North. On 18 May 2008, he was appointed manager of Conference South side Newport County, and guided the club into the Conference the following season. On 11 January 2011, Dean was appointed manager of League Two side Aldershot Town. 

Appearances

2002/2003 - squad number 9

D3	29.3.03	Exeter City (H)	as sub
D3	5.4.03	Bristol Rvrs (A)
D3	12.4.03	Lincoln City (H)	as sub
D3	19.4.03	Carlisle Utd (A)
D3	21.4.03	Macclesfield Tn (H)	2 goals
D3	26.4.03	Leyton Orient (A)
D3	3.5.03	Hartlepool Utd (H)	as sub