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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.

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 F.C., he got injured in April in a home match against Yeovil Town F.C.. 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 to football on the 9th of October when he came on as a second half sub in a Checkatrade Trophy group stage match VS Plymouth Argyle F.C., he scored within 10 minutes of returning he scored a goal to give Swindon Town F.C. a 3-0 lead which they held until the 90 minutes was finished.

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.

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.

He began his career at Maidstone United before being signed by Tamworth. He was loaned out to Maidstone United and Stafford Rangers before being signed by Bolton Wanderers for £10,000 in August 2014. He was loaned out to Notts County F.C. in January 2015. He then joined Wigan Athletic at the start of the 2016/17 season however he only played once and got loaned out Forest Green Rovers F.C. and he helped them get promoted scoring twice in the final. At the end of the season he joined Swindon Town F.C. on a permanent deal.

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.

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.

Kaiyne River Woolery (born 11 January 1995) is an English professional footballer who plays as a striker for League Two club Swindon Town.