The youngster came through the Academy ranks at Cobham, featuring in the same youth team as the likes of Mason Mount, Tammy Abraham and Ruben Loftus-Cheek and training on many occasions with the senior side under Antonio Conte.
However a succession of injuries, a freak illness and the Covid-19 pandemic hitting have seen him depart Chelsea and move into non-league via a short spell at Coventry.
The midfielder spoke to Goal on how he hopes a move to National League side Yeovil can get his career back on track, as well as opening up on his time at Chelsea.
‘I was playing at Chelsea, 18-years-old, everything was going well, and heading into the Under-23s having won a lot of trophies,’ Wakefield told Goal. ‘I played in unbelievable teams with the likes of Mason Mount, Andreas Christensen, Ruben Loftus-Cheek and many more. Everything was good.
‘I was a Chelsea fan before I signed for them. I used to get goosebumps on Champions League nights. All of a sudden, injuries started. I have had 10 hamstring injuries between the ages of 18 and 21.
‘I then had a collapsed lung which came on top of the hamstring injuries. I had 10 days off to go on holiday so I went to New York with my girlfriend. The plane journey led to me suffering a collapsed lung on the drive to my first training session upon my return.
‘I was rushed to hospital from the training ground and I had to have two months out with no exercise after that.
‘It has been a rollercoaster, but it makes me feel bulletproof. I want to be someone footballers can reach out to because I have been there. I am still just 23, but I have gone through a lot.’