Gillett made his Yeovil Town debut in the opening game of the season, making his first start and playing 90 minutes, in a 3–0 loss against his former club, Doncaster Rovers. Three days later, Gillett scored his first Yeovil Town goal in the first round of League Cup, in a 2–1 loss against Gillingham. However, Gillett suffered an injury that kept him out throughout September. After making his first team return in a 2–0 against Milton Keynes Dons on 4 October 2014, Gillett then scored his first league goal on 13 December 2014, in a 4–0 win over Oldham Athletic and three days later, on 16 December 2014, Gillett scored again in the second round replay, in a 2–0 win over Accrington Stanley Gillett continued to be in the first team until he suffered a knee injury that kept him out for the rest of the season.