Career
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 N ottinghamshire 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 2013-2014 season. He was loaned back to Maidstone in January 2014 for a two-month spell.
He joined Championship club Bolton Wanderers in August 2014 for a £10,000 fee. He was sent out on loan to League One side N ottinghamshire 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.