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On 31 January 2019, Bennett joined Swindon Town on loan until the end of the 2018–19 season.

On 31 January 2018, Bennett left Portsmouth by mutual consent.

On 1 February 2018, Bennett joined Bristol Rovers on a free transfer after leaving Portsmouth. He made his debut on the 3 February, replacing Ollie Clarke in the 56th minute of a 2–1 defeat to Shrewsbury Town. He made his first start a week later and scored the equaliser in a 2–1 comeback victory against Oxford United.

On 16 May 2017 Bennett signed a new three-year contract at Portsmouth keeping him at the club until 2020. In August 2017 he reached the milestone of 100 appearances for Portsmouth.

On 21 May 2015, Bennett signed for Portsmouth on a two-year contract, becoming Paul Cook's first signing as manager. Manager Dickov felt Bennett was badly advised to his move to Portsmouth.

On 8 August 2015 Kyle made his Portsmouth debut at home to Dagenham & Redbridge, scoring twice and assisting Gareth Evans before being substituted to a standing ovation by the Pompey fans.

After spending the 2013–14 season on loan and making three appearance for Doncaster Rovers, Bennett made his return to the first team, coming on as a substitute for Harry Forrester, in the 90th minutes, in a 3–0 win over Yeovil Town. Bennett scored his first goal of the season in the next game, in a 3–1 loss against Port Vale. A week later on 23 August 2014, Bennett scored his second goal of the season, in a 1–0 win over Colchester United. His third goal came on 20 September 2014, in a 3–2 win over Chesterfield. His fourth goal came on 22 November 2014, as well as, making an assist, in a 3–1 win over Rochdale. His fifth goal then came on 14 February 2015, in a 3–0 win over Yeovil Town. Bennett then scored his first brace of the season, in a 3–2 loss against Sheffield United on 7 April 2015, followed up the next game four days later against Rochdale. On the last game of the season, Bennett provided a double assist, in a 5–2 win over Scunthorpe United. Bennett finished the season, as he made forty-nine appearance and scoring eight times in all competitions. Bennett felt that his days at Doncaster Rovers would be over if the takeover had failed and giving him a chance to play in the first team.

On 24 January 2014, Bennett joined Bradford City on loan until the end of the season. He made his debut four days later, and was sent off in the 25th minute after clashing with Neil Kilkenny in a 0–0 draw at home to Preston North End. He scored his first goal for the club on 11 March, in a 2–0 win away against Colchester United. At the end of the 2013–14 season, Bennett scored once in eighteen appearance for the club. Bennett said his loan spell at Bradford City helped him with good experience, as well as, helping him grow up.

Ahead of the 2012–13 season, Bennett was soon linked with a move away from the club, prompting Manager Dean Saunders stated he started contract talk with Bennett. Bennett started well when he played 120 minutes in the first round of Football League Cup against York City and scored one of the penalties in the shoot-out, as Doncaster Rovers went through to the next round. Bennett then scored two goals in the first two games against Walsall and his former club, Bury. Bennett soon suffered a knee injury after facing a fitness test. After missing seven matches, Bennett made his return in a 1–1 draw against Swindon Town. Soon after, Bennett's poor performance against Bury on 2 February 2013 led the club's supporters criticising him, prompting Manager Brian Flynn to defend him. Weeks later on 26 February 2013, Bennett scored his first goal since returning from injury, in a 2–1 win over Shrewsbury Town. Bennett went on to make thirty-eight appearance and scoring three times in all competitions. Despite spending some of the half on the bench and injuries, Bennett was offered a new contract by the club and signed a two-year contract on 8 July 2013.

The 2013–14 season saw Bennett have his playing time restricted at Doncaster Rovers and joined Crawley Town on a one-month loan deal on 25 October 2013. Bennett was previously on the verge of joining Notts County on loan, but the move was rejected. Bennett made his Crawley Town debut the next day, in a 2–0 loss against Stevenage. Following his debut, Manager Paul Dickov made hints that Bennett could stay at the club for another month. Instead, Bennett returned to his parent club after making six appearance.

In May 2011 he was offered a new contract by the club but the beginning of July the club confirmed he has rejected the deal in favour of a move to Doncaster Rovers, and as the clubs could not agree on a transfer fee that it would go to a transfer tribunal to determine a transfer fee. In September 2011, the transfer tribunal was concluded that Doncaster Rovers were ordered by tribunal panel to pay Bury £180,000 in compensation.

Bennett made his Doncaster Rovers debut, in the opening game of the season, coming on as a substitute for Ryan Mason in the 75th minutes, in a 2–1 loss against Brighton & Hove Albion. Bennett then scored his first Doncaster Rovers goal in the first round of League Cup, in a 3–0 win over Tranmere Rovers three days later. Bennett then scored his first Doncaster Rovers league goal, in a 2–1 win over Peterborough United on 1 October 2011. Sky Sports reporter was impressed with his performance, quoting: "Kyle Bennett's introduction added pace and purpose to Donny's perspiration and the youngster deserved his clinical breakaway goal." His second goal then came on 2 January 2012 in a 2–0 win over Barnsley. Bennett's third goal later came in a 2–1 win over Nottingham Forest on 6 March 2012, followed up a week later on 13 March 2012, in a 1–1 draw against Reading. In his first season at the club, the club was relegated to League One after six seasons in Championship. Bennett's goal against Peterborough United soon earned him award of the club's Goal of the Year, though he was disappointed the club being relegated. In his first season at the club, Bennett made 39 appearance and scoring five times, in all competitions.

In March 2010 he had a two-week trial with Leicester City and then given a trial at Port Vale. At the end of the 2009–10 season, Bennett was released by the club.

In August 2010 he joined League Two club Bury on a one-year deal, after impressing on trial.

He made his debut in a 1–0 defeat to Port Vale at Gigg Lane on 7 August 2010. He scored his first goals in professional football on 26 February 2011, when he scored twice as Bury beat Crewe Alexandra 3–1. In his first season at Bury, Bennett scored two goals in thirty-three appearance in all competitions, as he helped Bury promoted to League One.

Bennett began playing for Wolverhampton Wanderers at the age of seven, signing for the club at age nine. He signed a three-year professional contract in September 2007, just after has seventeenth birthday. He stayed at Molineux for two years without ever making the first team. On 10 March 2009, Bennett signed his first professional contract with the club.

Kyle Bennett (born 9 September 1990) is an English footballer who plays as a midfielder for Bristol Rovers. He is the younger brother of footballer Elliott Bennett.