Here we go! Aston Villa star makes shock move to Olympiacos

Leon Bailey is preparing for an unexpected new chapter in his career.

Details: According to renowned insider Fabrizio Romano, Olympiacos have reached a verbal agreement to sign Aston Villa winger Leon Bailey on a permanent transfer. Romano has already given the deal his famous here we go, with Aston Villa providing the green light for the move to proceed.

• Also read: Can Osnabrück withstand the holders? Prediction for Osnabrück vs Bayern Munich - 02.09.2026

The Jamaican winger is now on his way to Athens, where he is expected to undergo medical tests before completing the final formalities of the transfer. If everything goes according to plan, Bailey will sign a contract with the Greek giants running until June 2029.

The move comes as a surprise after Bailey's lengthy spell in English football. The 29-year-old joined Aston Villa in the summer of 2021 and went on to make more than 160 appearances for the Birmingham club. Last season also included a loan spell at Roma, which was cut short in January 2026 before the winger returned to Villa.

It is worth noting that Bailey made 30 appearances across Aston Villa and Roma last season, scoring one goal and providing one assist. The Jamaica international is now set to continue his career in Greece after Olympiacos moved quickly to secure a permanent agreement.

Reminder: Official! Aston Villa announce signing of Harwood-Bellis for €29.2m