Football Italia
·2 September 2025
Report: Milan consider swoop for former Manchester United and Spurs free agent

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·2 September 2025
Milan are considering a dramatic move for free agent Sergio Reguilon, as reports from Italy claim the player’s representatives have contacted the Rossoneri in hopes to convince them to take on the experienced defender to improve squad depth.
According to what has been reported by CalcioMercato, via MilanNews24, Massimiliano Allegri’s side may not be done in the transfer market – despite the window slamming shut yesterday evening.
LA SPEZIA, ITALY – APRIL 14: Igli Tare of SS Lazio looks on during the Serie A match between Spezia Calcio and SS Lazio at Stadio Alberto Picco on April 14, 2023 in La Spezia, Italy. (Photo by Gabriele Maltinti/Getty Images)
The reports claim that whilst negotiations are not currently in progress, a move cannot be ruled out if Allegri asks sporting director Igli Tare for the additional reinforcement.
Sergio Reguilon has become a bit of a journeyman, playing for six different clubs in the last six years. The 28-year-old, who started his career at Real Madrid, spent the 2019-20 season on loan with Sevilla where he won the Europa League before signing for Tottenham Hotspur in the same summer.
epa10879542 Luca Koleosho (R) of Burnley in action against Sergio Reguilon of Manchester United during the English Premier League soccer match between Burnley FC and Manchester United, in Burnley, Britain, 23 September 2023. EPA-EFE/PETER POWELL
His spell with the North London side was mixed, playing 67 times in all competitions across two seasons before being loaned out to Atlético Madrid, Manchester United and Brentford in the 2022-23 and 2023-24 campaigns.
Reguilon returned to Spurs last season but played just six times in all competitions and left the club as a free agent when his contract expired in the summer.