29-Year-Old Aston Villa Star Set For Surprise Exit After Failed Hull Move: Right Move For The Midlands Club? | OneFootball

Aston Villa are now close to seeing Leon Bailey leave for Olympiacos after the British transfer window shut on 1 September. The Daily Express reports that the winger has found an alternative route out of Villa Park after a proposed move to Hull City collapsed late in the window.

Aston Villa face an exit for 29-year-old winger Leon Bailey after the UK transfer window ended

Bailey had been left training alone at Bodymoor Heath after that failed switch, showing how far he had slipped from Unai Emery‘s plans. Now Olympiacos have stepped in with a permanent deal, and the winger is heading to Athens for a medical before completing the move. Reports indicate he will sign a contract running until June 2029.

Villa can no longer replace him from the English market, yet the club can still clear a difficult situation. Bailey’s departure closes a chapter that had lost momentum.

T4O take: Why Aston Villa needed a permanent sale

Bailey’s best spell came in 2023/24, when he produced 10 Premier League goals and 10 assists, but that output has fallen away sharply. Across the 2024/25 and 2025/26 league campaigns, he scored just one goal. Last season brought 13 league appearances, mostly from the bench, with zero goals and one assist, while his spell at Roma produced seven Serie A appearances without a goal.

PORTO, PORTUGAL – JULY 25: Leon Bailey of Aston Villa during a pre-season friendly match between FC Porto and Aston Villa at Estadio do Dragao on July 25, 2026 in Porto, Portugal. (Photo by Octavio Passos/Getty Images)

For Aston Villa, those numbers matter more than memories of his peak. Emery needs wide players who can deliver consistently, and Bailey has become too unreliable to justify a key role.

Why the Olympiacos move suits Aston Villa

Keeping a player who had been frozen out and was training separately made little sporting sense. Villa needed to end the uncertainty, reduce the wage burden and clear space around Emery’s plans, even without an immediate replacement.

The failed Hull move could have trapped the club in an awkward situation, but Olympiacos have offered another route. Bailey gets a fresh start, while Aston Villa remove a stalled relationship from the squad. His 2023/24 numbers deserve respect, yet they now look like an exception rather than a trend, and that makes this exit sensible.