Jermaine is a quick winger who began his career as a youth player with Tooting & Mitcham United before switching to the Staines Town youth setup. Moves to Kingstonian, Raynes Park Vale (loan), Merstham and Ashford Town followed before Jermaine enjoyed trials with Bristol Rovers, Hayes & Yeading and Southampton. He chose however to join Aldershot Town in the summer of 2010.
He made his professional debut against Watford in the League Cup and more recent success saw him win the man of the match award during Aldershot's cup tie versus Manchester United. He made 75 appearances for the Shots and scored five goals before signing for the Robins on Friday 20 January 2012 on a two and a half year contract.
The tricky winger made a big impact upon Cheltenham's season and scored two important goals against Torquay in both play-off semi-final legs to help book Cheltenham' spot at Wembley in the final. Much is expected from Jermaine who has quickly become a key player for the Robins.