He made his debut for AFC Bournemouth, away to Shrewsbury Town, in a 4–1 defeat in the League Two on 18 October 2008.[5]
Molesley signed for Exeter City on 18 January 2013. On 30 April 2013, he was released by Exeter due to the expiry of his contract.[6]
Managerial career
Molesley Began his coaching career in 2015 by coaching AFC Bournemouth under 15's.[7]
Whilst playing for Weymouth in 2016, Molesley became a player-coach for the team.[8]
Molesley became the manager of League Two club Southend United on 13 August 2020 on a three-year contract.[9] After seven months, on 9 April 2021 Molesley was sacked by Southend United following a period of poor results and the club in 23rd place in the league.[10]
On 20 September 2021, Molesley returned to Aldershot Town as manager on a deal until the end of the 2022–23 season. Tom Prodomo joined as assistant manager after previously working with Molesley at Weymouth and Southend. Molesley was also joined by Terry Brown who had previously managed both the Shots and Molesley himself.[11]
On 30 November 2022, Molesley was appointed Director of Football of Gosport Borough, taking control of the first-team as well as wider football operations.[13] He departed the club at the end of the season.[14]