Jamaican international Leon Bailey is closing in on a move to Greece after Olympiacos reached a verbal agreement with Aston Villa for the permanent transfer of the winger.
According to transfer journalist Fabrizio Romano, Olympiacos have received the green light from Aston Villa to complete the deal, with Bailey now travelling to Athens for his medical tests.
The 29-year-old is expected to sign a contract running until June 2029, bringing his time at Aston Villa closer to an end after five years with the Premier League club.
Bailey Heading To Athens
The move comes after a summer in which Bailey’s future at Villa had become increasingly uncertain.
Several clubs were linked with the Jamaican during the transfer window, including Hull City, Sevilla and Saudi Arabian sides, but Olympiacos emerged as the destination in the final stages.
Romano’s latest update indicates that the Greek club has now agreed terms with Villa and is moving ahead with the transfer. Bailey’s medical in Athens is the remaining major step before the move can be formally completed.
From Aston Villa To Olympiacos
Bailey joined Aston Villa from Bayer Leverkusen in 2021 and established himself as an important attacking option during his time at Villa Park.
One of his most memorable moments came in December 2023 when he scored the only goal in Villa’s 1-0 victory over Manchester City. He was also part of the Villa team that reached the semi-finals of the UEFA Europa Conference League during the 2023/24 season.
Bailey spent part of the 2025/26 campaign on loan at AS Roma before returning to Aston Villa in January 2026 after the Italian club spell ended early.
His return did not lead to a long-term revival at Villa, however, and the club subsequently worked toward finding a permanent destination for the Jamaican winger.
A New European Chapter
A move to Olympiacos would give Bailey another opportunity to compete in European football while continuing a career that has taken him from Jamaica to Belgium, Germany, England and Italy.
The Greek giants are one of the country’s most successful clubs and regularly compete in European competitions, giving Bailey another platform to showcase his ability at the highest level.
For Jamaican football fans, the transfer represents another significant chapter in the career of one of the country’s most accomplished players.
Bailey’s move to Olympiacos is not officially complete yet, but with a verbal agreement in place and the winger travelling to Athens for his medical, his Aston Villa chapter appears to be coming to an end.