Olympiacos reach verbal agreement to sign Leon Bailey from Aston Villa

Olympiacos have reached a verbal agreement with Aston Villa to sign Leon Bailey on a permanent transfer, with the Jamaica international travelling to Athens to complete a medical.

Fabrizio Romano reports that Villa have given the deal the green light and that Bailey is expected to sign a contract running until June 2029 if the remaining formalities are completed.

Greek reports have independently confirmed that the 29-year-old is heading to Athens for medical checks and to finalise the transfer.

Neither Olympiacos nor Aston Villa have formally announced the move, and no sufficiently reliable transfer fee has yet emerged. The deal should therefore remain classified as advanced rather than complete.

Bailey has been with Villa since joining from Bayer Leverkusen in August 2021. His existing contract at Villa Park runs until June 2027, leaving the Premier League club in a position to sanction a permanent departure rather than risk allowing him to enter the final months of his deal next year.

The winger enjoyed his strongest campaign in England in 2023/24, scoring 14 goals in all competitions as Villa secured Champions League qualification. His role subsequently diminished, and he spent part of last season on loan at Roma after the Serie A club agreed a temporary move with an option to buy.

That spell did not develop into a permanent transfer and Bailey returned to Villa before the end of the campaign.

Olympiacos have now moved to offer him a long-term route away from Birmingham. The Jamaica international would bring Premier League, Bundesliga, Serie A and European experience to José Luis Mendilibar’s attacking options.

The transfer has progressed beyond initial talks: Olympiacos and Aston Villa have a verbal agreement, Bailey has been cleared to travel for his medical and terms through 2029 have been reported. Medical clearance, final paperwork and an official club announcement are still required before the move can be considered complete.