[2] As a youngster Fleetwood was a talented rugby union fly-half and was part of the Newent team that won the Gloucester Schools Cup.
[2] Fleetwood started his career at Cardiff City at the age of 12 when he joined the club's youth programme, and eventually made one first team appearance in two and a half seasons as a professional.
On 3 October 2005 Fleetwood was involved in a car accident on his way back from a Cardiff reserve match against Hereford United along with fellow players Nicky Fish, Lloyd Jenkins and Anthony Taylor.
Fleetwood was still suffering the psychological effects of his car crash earlier in the season[citation needed] and he was arrested near Ninian Park for drink-driving where he was found to have more than double the legal limit of alcohol in his blood; he was banned from driving for twenty months and fined £455.
[5] He signed for Hereford United in January 2006, who beat off competition from Hamilton Academical,[6] and made a good start, scoring four goals in five league games.
He featured as a substitute in the Conference play-off final win over Halifax Town, and subsequently signed a new one-year contract.
[11] In November and December he was a major factor in Forest Green causing an FA Cup upset when they knocked out Football League Two side Rotherham United.
[14] [15] This was soon followed up with a reported £200,000 offer from Charlton Athletic[16] On 20 January Forest Green Rovers announced that they had reached a financial agreement with Crewe Alexandra and had allowed Fleetwood to enter into talks with the League One side.
On 30 October 2008 Fleetwood agreed to join League One side Brighton & Hove Albion on loan, initially for one-month.
On 18 March 2009, Fleetwood signed on loan to Football League Two side Exeter City until the end of the 2008–09 season, where he impressed, scoring three goals in eight appearances.
Fleetwood made his long-awaited debut for Charlton Athletic away to Hereford United in the 2009-10 Football League Cup First Round, entering the field of play in the 82nd minute.
[25] On 1 September 2009 on transfer deadline day, Fleetwood returned to Exeter City on a season-long loan deal.
[26] He finished the season as the Bulls top scorer with 18 goals, helping the club to survive relegation from the Football League.
[29] The next week he made his full debut at home to Darlington; Luton won the game 2–0 with Fleetwood scoring one and setting up Danny Crow for the other.
[41] He scored his only goal for the club on 9 February 2016 in an FA Trophy extra time replay defeat against Bognor Regis Town.
[52] Fleetwood initially joined Gloucester City as the club's Head of Academy in March 2023,[53] before additionally taking on the role of first team coach later that year.