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 an short-term contract. ==Career statistics==