[2][3] After recovering from an injury, he made his Southampton first-team debut against Leicester City in the fourth round of the FA Cup in 2006, coming on for an Injured David Prutton after just 30 minutes of the game played.

[5] After his loan spell at Yeovil Town came to an end, Gillett made his league debut for the club, where he came on as a substitute for goal scorer Stern John in the late minutes, in a 1–0 win over Leicester City on 15 March 2008.

[8] 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.

[13] Even after making his return from injury, Gillettt was unable to help the club survive relegation in the Football League Championship.

[14] However, Gillett's first team opportunities became increasingly limited under the management of Alan Pardew and never played for the club again after his Johnstone Paint Cup final appearance.

[28] After making seven appearances and scoring once in total, Gillett returned to his parent club after suffering from ankle injury and in addition to being recalled.

[42] His second Doncaster debut came in a 2–0 win away to Preston North End; Gillett however, was sent off late on in the match, for two bookable offences.

[56] After missing out, due to injury,[57] Gillett made his Nottingham Forest debut, making first start and playing 90 minutes, in a 1–0 win over Bristol City.

[59] Gillett soon lost his first team place under the management of Alex McLeish and Billy Davies later in the season, as he made twenty–five appearances for the club.

[63] With first team opportunities at Nottingham Forest increasingly limited, it was announced on 31 October 2013, Gillett signed for League One side Bristol City on loan until 28 January 2014[64] Gillett made his Bristol City debut on 2 November 2013, where he came on as a substitute for Ryan Taylor, in a 1–1 draw Oldham Athletic.

[68] After serving a two match ban,[69] Gillett returned to the first team and scored his second Bristol City goal in the last game of the season, in a 1– 1 draw against Crawley Town.

[72] 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.

[73] Three days later, Gillett scored his first Yeovil Town goal in the first round of League Cup, in a 2–1 loss against Gillingham.

[82] Gillett then made his first appearance of the season on 30 January 2016, where he came on as a substitute for Liam Walsh in the 82nd minute, in a 3–2 win over Wimbledon.

[85] Gillett then extended his loan spell with Peterborough United until the end of April and went on to make five appearances for the club.