Career
From August 2006, he spent three months on loan to Blackpool. lieutenant was with the Fylde Coast club that he scored his first league goal, on 12 September, in a 1–1 draw with Chesterfield at Bloomfield Road. On 23 November 2006, he moved on loan to Bournemouth until the New Year.
On 30 January 2007, Gillett returned to Blackpool on loan until the end of the 2006-2007 season.
On 27 May 2007 he came on as a last-minute substitute in the Seasiders" League One play-off final victory over Yeovil Town at Wembley. On 20 September 2007, he joined Yeovil Town on loan, initially for a month.
He made his Southampton first-team debut against Leicester City in the 4th round of the Field Artillery Cup in 2006, coming on for an Injured David Prutton after just 30 minutes of the game played. Doncaster Rovers
He joined championship club Doncaster Rovers on 12 October 2009 on a two-month loan.
On 15 May 2010 he was released from Southampton.
On 5 July 2010, Gillett agreed to join Doncaster Rovers subject to a medical, with the deal being completed on the evening of 7 July. Gillett signed a 2-year contract with Doncaster, and was assigned the shirt number 18. On 18 September 2010 he scored his first goal for Doncaster in a 2–2 draw with Watford
Nottingham Forest
On 4 August 2012 it was announced he joined Nottingham Forest to team up with former Manager Sean O"Driscoll.
On 31 October 2013, Gillett signed for Bristol City on loan until 28 January 2014, subsequently extended to the end of the season.
Yeovil Town
On 7 August 2014, Gillett resigned for Yeovil Town on a two-year contract. On 5 March 2016, Gillett joined League One side Peterborough United on a one-month loan deal.