Just over 12 months ago the London-born striker was eyeing up games at Lowestoft, Guiseley, North Ferriby and Brackley while playing for ambitious Midlands club Tamworth in the sixth tier of the English pyramid.
The youngster had taken the tough route to professional football – persisting with his ambition despite never having been picked up in the academy system.
And last summer he found himself at the centre of a tug-of-war between two Lancashire rivals, as Wanderers battled Burnley for his signature.
Dougie Freedman won in the end, paying £10,000 to the Lambs, plus a pre-season friendly, but it is Neil Lennon who is now enjoying the fruits of his labour.
Woolery was the star of the show in the Whites’ pre-season opener at Atherton Collieries on Saturday, and scored in a 3-1 win over Spennymoor on Monday night.
But the 20-year-old, who made his Championship debut in the penultimate game of last season as a late substitute for Adam Le Fondre, admits he’s hungry for more.
“If someone would have told me 12 months ago that I’d have played in the Championship I wouldn’t have believed them,” he told The Bolton News.
“I’ve tasted the first team now so obviously I want to play more. If I’m not in the picture then I’d go and show the gaffer what I can do out on loan.
“I want to fight for a place. It doesn’t matter whether it’s a friendly, or whatever, you can’t take your foot off the gas.
“These games are the most important because the gaffer is there to see what your attitude is like.
“He believes in youth and that is a big thing when you’re looking to get through.”
Woolery acknowledges the debt he owes to his former club Tamworth, who welcome a Wanderers XI on July 25 for a pre-season friendly.
The pacy striker moved to the Midlands after a spell with Maidstone but has never worked within the academy system of a larger club.
“I always knew I wanted to be a footballer,” he said. “But it was a case of waiting for the right time and trying to take my chance.
“I’d never been in an academy and so I had to work that little bit harder.
“Tamworth was my first full-time club and they did a lot for me, the assistant manager Scott Lindsey especially, he brought me to the club and it all went from there.
“I’ll never forget what they did for me. I have a lot of respect because they put me in the shop window.”
Woolery spent a month on loan at Notts County last season, playing out on the wing for the majority of his stay at Meadow Lane, which totalled five appearances.
“It was good, I enjoyed it, but I’d prefer playing up front,” he admitted.
“Everyone there was great. It has been a difficult time for them but I was glad of the experience.”