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.[7]
On 6 February 2016, Woolery scored his first senior goal for Bolton, a 93rd-minute winner against Rotherham United.[8]
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 7 August 2017, Woolery joined League Two side Swindon Town on a three-year deal for a £350,000 fee.[11]
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.[12] 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.[13] He scored his first goal for Tranmere in an EFL Trophy tie against Wigan Athletic on 11 November 2020.[14]
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".[15] On 14 July 2022, Motherwell announced that Woolery had left the club to join TFF First League club Sakaryaspor for an undisclosed fee.[16]