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Bailey signed for The Lions from Tadcaster Albion for an undisclosed fee on 9th January 2021 after scoring eight goals in 12 appearances for The Brewers.
The youngster from Rossendale in Lancashire has a good youth pedigree having been involved with the Academy set ups at Manchester United, Accrington Stanley, Bury and Blackburn Rovers before getting a chance with Everton.
That was short-lived as Tranmere Rovers came in for him with a scholarship and then gave him his first pro contract. Bailey spent four years at Tranmere but with a squad ladened with very experienced players he found opportunities scarce, although he was in and around the first team. Most of his appearances came off the bench.
At the time of signing his contract the 6ft 4ins striker said: “I know Guiseley like to push young players through and progress them and I am looking forward to that. Tranmere were a very good club but chances were limited for me and due to Covid they had to off load players. I am just eager to be back playing as the last time I had a game for Tadcaster was a friendly before Christmas.”
Joint Manager Russ O’Neill said “Bailey fits our profile perfectly, he is young and hungry with bags of potential. He has adapted really well so far to non league football with lots of goals in a short space of time at Tadcaster. He has got all the attributes to become a real asset to our club and we look forward to watching him develop.”
On his 20th birthday on 7th June 2021 Bailey’s contract with the club was extended by a further season, on the extension Thompson said “It will be great to get back in training as I have a lot of unfinished business after getting just one game in after my transfer from Tadcaster Albion last Christmas. I made my debut at Gateshead and then that was it.”
“It will be great to catch up with some of the lads I played with at Everton, I am really pleased to be playing at Guiseley under Russ O’Neill and Marcus Bignot, they are great coaches and I think they will improve my game greatly.”
“I want to show the club and its supporters what I am capable of. I want to continue improving my game and I know that Russ and Marcus are the sort of managers who will push you to get the best out of you.”
“There will be a number of new faces in the squad and I am looking forward to meeting up with the lads and getting cracking on a new season, a season in which we will be hoping to be battling it out at the top end of the table.”