Jamaican international Leon Bailey has officially completed his move to Greek giants Olympiacos, bringing his five-year spell with Aston Villa to an end.
Olympiacos confirmed the signing on Wednesday, September 2, welcoming the Jamaican winger to the club after reaching an agreement with Aston Villa for his permanent transfer.
Bailey, who turned 29 in August, joins the Greek side after making 163 appearances for Aston Villa, scoring 23 goals and providing 25 assists. He also leaves England as a UEFA Europa League winner after Villa lifted the trophy during the 2025/26 season.
Bailey Begins New Chapter In Greece
The move gives Bailey a fresh start after a difficult final period at Villa Park.
He initially joined Aston Villa from Bayer Leverkusen in 2021 and quickly became an important part of the club’s attack. His best period came during the 2023/24 campaign, when he produced some of his most impressive numbers in a Villa shirt as the club secured Champions League qualification.
Bailey’s final years at Villa were less consistent, however. He spent part of the 2025/26 season on loan at AS Roma before returning to England in January, and his future remained uncertain as Villa reshaped their squad.
That uncertainty has now been resolved, with Olympiacos providing the Jamaican with his next destination.
A Career Across Europe
Olympiacos becomes the latest stop in a European career that has already taken Bailey through several major football leagues.
Before moving to Aston Villa, he established himself at Bayer Leverkusen in Germany after first making his name with Belgian club Genk. Olympiacos’ official announcement credits Bailey with 156 appearances, 39 goals and 25 assists for Leverkusen, while he made 77 appearances for Genk, scoring 15 goals and recording 19 assists.
He also had a spell with Roma, making 11 appearances during his time with the Italian club.
For Jamaica, Bailey has established himself as one of the country’s most recognizable players of his generation. Olympiacos lists him with 41 senior international appearances and 11 goals for the Reggae Boyz.
What Bailey Brings To Olympiacos
Olympiacos will be hoping Bailey can rediscover the form that made him such an influential attacking player during his strongest years at Aston Villa.
The Greek giants are one of the country’s biggest clubs and regularly compete on the European stage. Bailey’s experience in the Premier League, Bundesliga, Serie A and European competitions gives him a wealth of experience to bring to his new team.
His arrival also adds another experienced attacking option to an Olympiacos squad that has been busy strengthening ahead of the new season.
A New Journey For Jamaica’s Bailey
From his early days at Genk to becoming a Premier League player and European champion with Aston Villa, Bailey has built an impressive career far from home.
Now, Greece becomes the next destination.
With the transfer officially completed, Leon Bailey can turn his attention toward making an impact in the red and white of Olympiacos and beginning the next chapter of his European football journey.