Dean was born in Bishops Stortford on 15 June 1986 and started his football career with Ipswich Town as a trainee before being selected for the first team in 2003. After more than 70 appearances for Ipswich and numerous loans to other clubs, he signed for Yeovil in 2009, joining MK Dons as Karl Robinson’s first signing of the 2011/2012 season.
With 15 goals in all competitions, Dean was the Dons’ top scorer in his first season, despite primarily playing as a winger. In the 2012/13 season, he bagged 12 more to share top scorer honours with Ryan Lowe, although he scoring form was hampered by serious injury that caused him to miss the first half of the 2013/14 season. Dean scored his first hat-
Other notable appearances included scoring against QPR in the FA Cup 3rd Round in 2011/2012. He also scored a long range free kick in an FA Cup 3rd round replay win against Sheffield Wednesday at home in January 2013.
He was released in June 2017 after scoring a total of 37 goals in 192 appearances for the Dons and joined Northampton Town shortly afterwards.