The 2008–09 season saw Gillett's expectation to make a breakthrough in the first team under the management of Jan Poortvliet. Gillett made his first start for the club in the opening game of the season, playing 90 minutes, in a 2–1 loss against Cardiff City. He began to get first team football for numbers of games until he suffered injuries and suspension. Even after making his return from injury, Gillettt was unable to help the club survive relegation in the Football League Championship.