Kaiyne Woolery

Kaiyne River Woolery (born 11 January 1995) is an English professional footballer who plays as a winger for League of Ireland Premier Division club Sligo Rovers.

Career Early years Woolery was signed by Conference Premier team Tamworth from Isthmian League club Maidstone United in June 2013. He was loaned to Stafford Rangers of the Northern Premier League at the start of the 2013–14 season. He was loaned back to Maidstone in January 2014 for a two-month spell.

Bolton Wanderers He joined Championship club Bolton Wanderers in August 2014 for a £10,000 fee. He was sent out on loan to League One side Notts County in January 2015.

He made his Bolton debut as a substitute for Adam Le Fondre when Wanderers lost 3–0 to the eventual Champions Bournemouth on 27 April 2015. On 6 February 2016, Woolery scored his first senior goal for Bolton, a 93rd-minute winner against Rotherham United.

Wigan Athletic Woolery joined Wigan Athletic on 31 August 2016 and was given the number 18 shirt. He made his debut for the Latics on 3 December 2016, when he came on as a substitute for Max Power in the 86th minute in a 1–0 loss to Derby County.

On 21 January 2017 it was announced that Woolery had signed for National League side Forest Green Rovers on loan until the end of the season. He made his debut for Forest Green on the same day of his signing, coming on as a substitute for Keanu Marsh-Brown in a 1–1 draw with Braintree Town. Woolery went on to score twice for FGR at Wembley in the 2017 National league play-off final.

Swindon Town On 7 August 2017, Woolery joined League Two side Swindon Town on a three-year deal for a £350,000 fee. After coming on as a half-time substitute, he scored an equaliser against Exeter City on his Swindon Town debut at the County Ground on 12 August 2017. After a fairly inconsistent first season for Swindon Town, he got injured in April in a home match against Yeovil Town. This injury ruled him out for the rest of the 2017/18 season and the first 2 months of the 2018/19 season. He made his return on 9 October 2018, coming on as a second half sub in an EFL Trophy group stage match against Plymouth Argyle and scoring within ten minutes.

Tranmere Rovers On 14 September 2020, Woolery joined League Two side Tranmere Rovers on a free transfer. He scored his first goal for Tranmere in an EFL Trophy tie against Wigan Athletic on 11 November 2020.

Motherwell On 22 June 2021, Woolery signed for Scottish Premiership side Motherwell on a three-year contract, with the manager Graham Alexander quoted as saying, "Kaiyne is a player I've admired for a few years now". On 14 July 2022, Motherwell announced that Woolery had left the club to join TFF First League club Sakaryaspor for an undisclosed fee.

Ionikos In January 2023, Woolery joined Super League Greece side Ionikos on a free transfer.

Anorthosis Famagusta In June 2024, Woolery joined Cypriot First Division side Anorthosis Famagusta.

Tranmere Rovers On 30 January 2026, Woolery featured in a Finnish League Cup match on trial with Gnistan. However, on 20 March 2026, Woolery returned to former club Tranmere Rovers on a short-term contract. On 12 May 2026, the club announced he would be leaving in the summer once his contract expired.

Sligo Rovers On 13 August 2026, Woolery joined League of Ireland Premier Division club Sligo Rovers on a short-term deal until the end of the season.

Woolery made his debut for Sligo Rovers on 15 August 2026 in the Club Orange FAI Cup against Kerry FC, coming on as substitute in the second half and capped his first appearance off with scoring his first goal for the club and his first competitive goal in 1,364 days in the 91st minute.

Career statistics

Honours Swindon Town EFL League Two: 2019–20

Tranmere Rovers EFL Trophy runner-up: 2020–21