Josh Bayliss first started training at Sheffield Wednesday back in August, and since then he’s been a regular feature in the club’s U21s.

The former Gillingham youngster, who recently turned 20, was handed the opportunity to team up with the Owls at Middlewood Road last year, and will have been hoping that a successful spell there could lead to a professional contract in South Yorkshire.

Months, and several first team training sessions later, Bayliss is still part of the setup at Wednesday, despite a seemingly minute chance of actually being given a contract. He’s got 16 goals and assists in an Owls shirt so far, but his stay in Sheffield has been funded by his family – and he’s also believed to have picked up a coaching job on the side to help pay his way.

Josh Bayliss has been at Sheffield Wednesday for months

Wednesday have been in a bind this season when it comes to new arrivals, with the English Football League having to be consulted on any new wage that the club takes on board, and that has led to the attacking midfield man being left out in the cold when it comes to an actual contract.

The club have picked up a number of free agents and loans when they have been allowed to add to their squad, and it looks like 20-year-old Zain Silcott-Duberry will take up the final spot that they have left. That decision is likely to leave Bayliss in limbo for even longer, though he’s desperate to get his opportunity as an actual Sheffield Wednesday player.

In the early stages of his trial Bayliss was listed as a trialist when he was named in the club’s U21 XIs, but he’s been a named part of the side for several months now despite not being on Wednesday’s books. The youngster was part of first team training again as recently as this past weekend.

It remains to be seen how much longer the ex-Croydon loanee will be able to continue doing his thing for the U21s, but after picking up another assist on Friday he’s certainly played his part in the 2025/26 campaign. He’ll be hoping that a real chance – and a paying contract - is around the corner when the club have more freedom in the recruitment department.