Leon Bailey has completed a permanent move from Aston Villa to Olympiacos, ending a summer of uncertainty for the Jamaica international after Saudi Arabian clubs showed interest in signing him.
The Greek club confirmed the transfer on Thursday, 3 September, while Aston Villa had announced the departure the previous day. Bailey is understood to have agreed a contract with Olympiacos until June 2029 after travelling to Athens for a medical.
Al-Ittihad and Al-Diriyah had both explored a deal for the winger after the Premier League transfer window closed on 1 September. Saudi Arabia’s registration deadline was not due to pass until 6 September, leaving Villa with the possibility of completing an overseas transfer.
Leon Bailey completes Aston Villa exit
Those discussions ultimately came to nothing, with Olympiacos moving quickly to secure Bailey. The transfer represents a permanent solution for Villa, who had been seeking to move on the 29-year-old throughout the summer.
Bailey spent last season on loan at Roma but made only 11 appearances before returning to Villa Park. With manager Unai Emery no longer appearing to regard him as part of his plans, another season on the fringes was unlikely to benefit either party.
Villa have significantly reshaped their attacking options during the summer, further reducing Bailey’s prospects of regular first-team football. His previous contract was due to run until June 2027.
The winger joined Villa from Bayer Leverkusen in 2021 and made 163 appearances for the club, scoring 23 goals and providing 25 assists. He enjoyed his most productive campaign in 2023-24, when he scored 14 times and helped Villa qualify for the Champions League.
Olympiacos also highlighted Bailey’s contribution to Villa’s Europa League success in the 2025-26 season as they welcomed him to Greece. The move gives him the opportunity to revive his career away from the Premier League, while Villa remove a senior player from their wage bill and clear space within Emery’s squad.
