Despite signing a new contract in August 2007, Gillespie handed in a transfer request in the summer of 2008 after having an impressive season with Cheltenham as they finished in mid-table in League One.
[1] Less than a week after handing in the request, Gillespie was sold to fellow League One club Colchester United for a fee of £400,000.
Unfortunately for both Gillespie and Colchester, however, his time with the club was dogged by injuries from shortly after his arrival, despite having made a promising start with three goals from his first three outings.
[4] The season was a huge shame for Gillespie who would have wished to make a much more impressive impact on his arrival as the club's record signing.
[8] Gillespie returned to Cheltenham Town on loan from Fleetwood on 15 August 2013, making his second debut for the club two days later in their 3–1 home defeat to Plymouth Argyle.
He scored his first goal for Rovers with an 88th-minute equaliser against Scunthorpe United after coming on as a 53rd minute substitution for the injured Alan Gow.