Several reports emerged on 2 September suggesting Leon Bailey could depart Aston Villa even though the Premier League summer window had already shut the previous evening. Sport Witness, drawing on Greek outlet Nova Sports, stated that Olympiacos had identified the forward as a priority target and opened discussions with Unai Emery's staff. That report described the Greek side as acting quickly to secure his signature before their own domestic deadline.
Football Insider wrote that two teams from the Saudi Pro League — Diriyah Club and Al Ittihad — had registered interest in the winger. The outlet framed the situation as time-sensitive, noting a 6 September cut-off for registrations outside England. No fee was mentioned by any of the publications covering the story.
Sports Mole took a slightly different angle, claiming an unnamed Champions League participant was preparing what it called a surprise agreement with Villa. The publication did not identify the buying club or provide further financial detail. Aston Villa have not commented publicly on any of these claims.
With the English market closed until January 2027, any potential exit would have required completion under the registration rules of another league. The various reports offered differing destinations but agreed that the forward was available for discussion immediately after the domestic deadline passed.
