(Credit: Imago)

Evan Shaw

Sun 29 March 2026 15:00, UK

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Destiny Udogie’s future has potentially never been so uncertain, with Tottenham Hotspur lining up a summer swoop for AC Milan star Pervis Estupinan.

The left-back has only been with the Serie A giants for one season after making the switch from Brighton last summer, but he could already be on the move again at the end of the campaign, as the Milan hierarchy are unconvinced by him.

Tottenham are showing a serious interest in bringing the former Brighton defender back to England next season, despite their Premier League status still hanging in the balance at the moment.

The 28-year-old has started just 12 league games for the Rossoneri since he joined their ranks, and as a result, the Italian side have already given the green light to the idea of selling him this summer.

Tottenham’s transfer plans will be heavily dictated by which league they find themselves in for next term, but Estupinan is a clear target if they are ultimately able to beat the drop.

Pervis Estupinan interest shows Tottenham feelings on Destiny Udogie

Estupinan could be a bargain transfer for Spurs this summer, as Milan are set to make him available for just £12.1million (€14m), according to Calcio Mercato.

That is surely a hugely enticing price for a player who was one of the Premier League’s highest-rated left-backs before he made the decision to try his hand in Serie A last summer.

While the Lilywhites’ pursuit of the Ecuadorian is only likely to be truly possible if they secure their top-flight status for next term, it is also a damning reflection of their feelings towards Udogie.

The 23-year-old has been consistently linked with a move away from North London in almost every transfer window in recent seasons, and this could finally be the time that his departure comes to fruition.

Injuries have plagued him again this term, as he has only been fit enough to start eight league games, with Djed Spence often filling in on the left side of defence.

The fact that Spurs are now taking interest in other potential options to fill that role is surely a clear indication that they are prepared to let Udogie go next season, regardless of which division they find themselves in.

Where could Udogie move to?

Former Manchester United chief scout Mick Brown recently told Football Insider that Manchester City have held talks about signing Udogie behind the scenes.

Pep Guardiola and Co. are keen to target further additions in the full-back areas ahead of next season, and the Spurs man is one of a number of candidates that they have identified on the left.

Brown revealed that the Citizens “know everything about” Udogie, and have been viewing him as a long-term target for several years now.

There is a distinct possibility that they could make a move to bring him in this summer, but it remains to be seen whether he will ultimately come out on top compared to their other targets.

If a move to the Etihad Stadium doesn’t materialise, then it would be no surprise if he had plenty of Serie A suitors once again, just as he has in recent windows.