The announced goodbye of Leon Bailey

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UEFA Europa League

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Olympiacos Jagiellonia Bialystok

16/09/26 21:00:00

1.36 4.33 7.50

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Leon Bailey, a 29-year-old winger, is on the verge of becoming a new player for Olympiacos after the Greek club reached a verbal agreement with Aston Villa for his permanent transfer. The deal takes place on this 2nd of September, following the closure of the transfer window in several major European leagues, and the Jamaican is already heading to Athens for his medical examination.

The agreement includes a contract until June 2029. Fabrizio Romano confirmed that Aston Villa has given the green light to complete the deal, although the amount the English club will receive for the transfer has not been disclosed yet.

Leon Bailey swaps the Premier League for Olympiacos

Bailey was under contract with Aston Villa until 30th June 2027, after renewing with the English club in February 2024. He arrived in Birmingham in 2021 from Bayer Leverkusen for around 25 million pounds.

Bailey's performance had diminished within the squad. In the 2025/26 Premier League season, Bailey played 13 games, with 3 starts, 459 minutes, 0 goals, and 1 assist. Also, during that same season, he had a stint at Roma, where he played 7 Serie A matches without scoring or assisting.

His time at Aston Villa includes 123 league appearances with 16 goals and 17 assists, according to available records. His best season in England was 2023/24, where he achieved 10 goals and 9 assists in 35 Premier League games.

Bailey's market value was at 14 million euros in the last Transfermarkt update in June 2026. The player also has 41 caps and 7 goals for Jamaica.

Olympiacos speeds up after signing Gustavo Puerta

Bailey's move comes after Olympiacos also completed the signing of Gustavo Puerta. The Greek club announced on this 2nd of September the addition of the 23-year-old Colombian midfielder from Racing de Santander, in a deal closing at 16 million euros according to market records.

Puerta, aged 23, played 36 matches for Racing, scoring 3 goals and providing 1 assist, before joining Olympiacos. The Colombian was also a starter in all matches for his national team until the round of 16 of the 2026 World Cup.

For Bailey, Olympiacos marks a new destination after his spells at Genk, Bayer Leverkusen, Aston Villa, and Roma. The Greek club now offers him a three-year deal until 2029, as Aston Villa definitively closes a chapter that began five years ago.

The next step will be the medical examination in Athens. If Bailey clears the tests, Olympiacos can finalize his arrival and complete the permanent transfer from Aston Villa, with a contract extending until June 2029.

This news is an automatic translation. You can read the original news, El adiós anunciado de Leon Bailey