Aston Villa FC are set to part ways with Leon Bailey in a surprise late move, as Olympiacos FC have reached a verbal agreement to sign the Jamaican winger on a permanent deal. According to transfer insider Fabrizio Romano, the Leon Bailey transfer has received the green light from the Premier League, with the 28-year-old already en route to Athens to complete his medical before finalising terms.
Leon Bailey Transfer: Deal Details and Contract Terms
The Aston Villa transfer saga took an unexpected turn late in the summer window as reports confirmed the Greek champions had struck a verbal agreement for a permanent transfer. Bailey is reportedly set to sign a contract running until June 2029, tying him to Piraeus for close to four years.
While official financial figures, including the transfer fee and Bailey’s projected salary at Olympiacos, have not yet been disclosed by either club, Aston Villa has already given clearance for the move to proceed, signalling the Midlands club’s willingness to cash in on the winger before the European transfer window closes.
Leon Bailey’s Journey and Villa Career So Far
Leon Bailey joined Aston Villa FC in 2021 from Bayer Leverkusen and went on to make 110 Premier League appearances, contributing 16 goals and 17 assists. His standout campaign came in 2023-24, when he scored 10 goals and registered nine assists as Villa qualified for the UEFA Champions League. Only Ollie Watkins had scored more goals than Bailey that season.
However, persistent injury troubles disrupted his rhythm, and Bailey spent the 2025-26 campaign on loan at Roma under Gian Piero Gasperini, becoming the Giallorossi’s first-ever Jamaican player.
What Does Leon Bailey Transfer Mean for Olympiacos?
For Olympiacos FC, landing a Premier League-tested wide forward marks a statement of intent as they push for continued domestic and European relevance. Bailey’s pace, dribbling and goal threat should bolster their attacking options significantly.
As the Leon Bailey transfer edges toward completion, all eyes now turn to Athens, where medical tests will determine the final step before an official announcement from Olympiacos FC and Aston Villa.
