Olympiacos made a splash, reached an agreement on all terms with Leon Bailey, and the 29-year-old Aston Villa winger is “heading” to Greece to sign a three-year contract. Very quickly, the Piraeus club set the wheels in motion and, following the signing of Puerta, are adding a major name to their roster for the 2026–27 season.
Transfer expert Fabrizio Romano dropped the “bombshell” at noon on Wednesday (September 2), noting that the player has agreed to a contract through 2029 and is coming to Greece to undergo a physical and formally complete his transfer.
EXCLUSIVE: Olympiacos reach verbal agreement for a surprise deal to sign Leon Bailey—here we go!
Permanent transfer from Aston Villa and a contract through June 2029. Green light to proceed from #AVFC.
AdvertisementBailey is on his way to Athens now for medical exams. pic.twitter.com/OI0e0jiVeR
— Fabrizio Romano (@FabrizioRomano) September 2, 2026
*photo source: AP


EXCLUSIVE: Olympiacos reach verbal agreement for a surprise deal to sign Leon Bailey—here we go!
