Tottenham handed Destiny Udogie boost as AC Milan agree Pervis Estupinan deal

Originally posted on To The Lane And Back
By Rohan Sengupta | Last updated Jul 22, 2025 8:14 PM ET

Tottenham receive surprise boost to keep hold of Destiny Udogie after AC Milan agree deal with Brighton for Pervis Estupinan

Several key Tottenham Hotspur players failed to hit the expected heights consistently throughout the 2024-25 campaign, thanks to a combination of injury problems and lack of team balance, but many big names stepped up towards the end as the North Londoners ended their 17-year trophy drought by lifting the Europa League trophy in Bilbao.

One of those players was Destiny Udogie, who played a crucial role in the club’s European success from the quarterfinals’ stage after struggling for consistency earlier in the season, and for some periods, even losing his left-back spot to Djed Spence. He also spent over a month on the sidelines following a hamstring injury, which hampered his progress.

Since officially arriving at Spurs in the summer of 2023, Destiny Udogie has made the left-back position his own. Owing to his tenacious, committed and creative displays, he became one of the first names on former boss Ange Postecoglou’s teamsheet. Thus, unsurprisingly, several clubs in Italy have been impressed by the full-back’s performances.

⚫️ Pervis Estupiñán will travel to Italy this week to sign a five year deal as
new AC Milan player.

Deal done since yesterday. ✅ pic.twitter.com/xcZk5wIdU7
— Fabrizio Romano (@FabrizioRomano) July 22, 2025

AC Milan have shown an interest in Udogie, viewing him as a potential replacement for Theo Hernandez. And as per certain reports, the Spurs star has been keen on a move to AC Milan as the chance to play under the decorated manager Max Allegri and in front of the iconic San Siro faithful entices him.

However, a recent transfer development has poured cold water on the Italy international’s hopes of sealing a switch to the Rossoneri.

Tottenham receive surprise boost to keep hold of Destiny Udogie amid Milan links

Now, according to transfer news expert Fabrizio Romano on X, AC Milan have moved on to agree a deal with Brighton and Hove Albion for Pervis Estupinan. The left-back will travel to Italy later this week to complete his medical and sign a five-year contract with Milan.

This may come as a setback to Udogie’s hopes of moving back to Italy and playing for one of the biggest clubs across Europe, as Pervis Estupinan is set to be brought in to replace Hernandez, who has already left for the Saudi Pro League. The Verona-born talent has a contract at N17 until 2030 and is considered a big part of the club’s future plans. Perhaps, given Tottenham were demanding a fee in the region of €50-60million to sell Udogie, the Rossoneri decided to pursue Estupinan.

From Tottenham’s perspective, Milan signing the Brighton man provides them with a big boost to keep hold of Udogie. The Italian is one of the club’s most exciting young players, and he has all the required qualities to become one of the Premier League’s best left-backs in the future. As such, Levy and Co. must do everything within their powers to retain his services.

This article first appeared on To The Lane And Back and was syndicated with permission.

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