Sheffield Wednesday have secured the signing of highly rated Lincoln City academy midfielder Denny Oliver for their U21 squad.
The 18-year-old moves to Hillsborough after impressing on trial, reuniting with former Imps academy chief Jonathan Pepper.
Owls Swoop for Local Prospect as Academy Links Pay Off
The move reunites Oliver with Sheffield Wednesday’s Academy Manager Jon Pepper, who previously worked at Lincoln before joining the Owls in December 2024. Pepper is understood to have been a key influence in the decision to bring Oliver across from Sincil Bank.
Oliver has been a mainstay in the Imps’ U18 side, even captaining the team in 2025. He showcased his talent in the FA Youth Cup, including a memorable last-minute winner away at Bolton Wanderers. His performances also earned him a spot on the bench in EFL Trophy fixtures and a short work experience loan with Grantham Town.
Speaking about his footballing journey earlier this year, Oliver described what it meant for his family, as all three brothers – Denny, Lewy and 14-year-old Kenzie – earned scholarship deals with Lincoln. In a special moment, all three were involved in the FA Youth Cup squad that reached the fourth round, where Lincoln were narrowly beaten on penalties by Plymouth Argyle.
Denny reflected at the time,
“It’s a really proud moment for us all. Kenzie is only 14 years old so to get a pre-scholarship at that age is really impressive for him. It makes me, Lewy and the whole family really proud – especially me and Lewy as we know how hard it is to achieve that at such a young age.”
Lincoln City’s director of football Jez George confirmed the move, stating,
“We are absolutely delighted that one of those players, Denny Oliver, has already secured a contract with a Category 2 club, which will give him more time to develop within an U21 environment.”
Oliver’s deep-lying role and ability to dictate tempo have drawn praise from academy observers, and his passing range and maturity on the ball make him a natural fit in development squads. With Wednesday keen to bolster their youth ranks, his signing is seen as a smart piece of recruitment.
Writer’s View
Denny Oliver’s switch to Sheffield Wednesday is a classic example of academy continuity bearing fruit. The link with former Imps staff member Jonathan Pepper clearly helped smooth the transition, and Oliver now has the opportunity to further his development in a Category 2 environment.
For Lincoln, it’s another sign of their academy’s growing reputation, while Wednesday fans can look forward to watching a composed, tactically mature midfielder progress through the ranks.
