[6] 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 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.
[9] 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.
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.
[14] 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".