Kaiyne Woolery

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…

As of match played 30 April 2022

Swindon Town

EFL League Two: 2019–20 Tranmere Rovers

EFL Trophy runner-up: 2020–21