Chelsea's Tosin Adarabioyo and Tottenham manager Roberto De Zerbi
Tosin Adarabioyo and Roberto De ZerbiImago

Why Roberto De Zerbi wants to sign Tosin Adarabioyo in rare Tottenham raid on Chelsea

James Barker

Senior Correspondent AUTHORITY Senior sports journalist with editorial experience at Football League World. FOCUS Statistical analysis and long-form opinion across the Breaking Media network. THE INSIGHT James utilises data and a network of club contacts to deliver verified, expert analysis. He provides the statistical depth and editorial judgment behind the stories to ensure fans get the full picture

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Tottenham Hotspur seem to have identified Tosin Adarabioyo as a potential Kevin Danso replacement.

Spurs are still looking to do business in these final hours of the transfer window.

Tottenham are widely reported to be pushing to sign Everton winger Iliman Ndiaye before Tuesday's 11pm deadline.

Whether his potential arrival would signal the end of the Lilywhites' incoming business remains to be seen.

Much of that could depend on what happens with Danso, as his possible exit could open up a long-desired transfer door for Roberto De Zerbi.

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Why Tosin Adarabioyo wouldn't be panic buy for Roberto De Zerbi

It was reported earlier on Monday that Sunderland are still pushing hard to sign Danso from Tottenham, with the defender keen to explore a move.

Sky Sports now claim that the Austrian has indeed requested to leave N17, along with two other players.

It's reported that Spurs have plans in place to deal with those potential exits, and that includes bringing Tosin in as De Zerbi's first choice.

The Sky Sports report states that De Zerbi has a long-standing interest in the Chelsea defender, having wanted to sign him for Brighton and Marseille.

Chelsea would reportedly be willing to answer the phone to offers for the 28-year-old, who hasn't played a competitive minute so far in 2026-27.

These two London rivals are seldom seen doing transfer business together, but when was the last time it happened?

Chelsea's Tosin Adarabioyo and Tottenham manager Roberto De Zerbi
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Who was the last player to be transferred between Spurs and Chelsea?

There's more than just a bitter inter-city hatred as to why Tottenham and Chelsea rarely do business with one another.

During Roman Abramovich's tenure as Chelsea owner (2003-2022), he made it explicitly clear that the Blues wouldn't do business with Spurs.

Albeit never a written rule, it was very largely stuck to, but one exception was made in January 2009.

This was when goalkeeper Carlo Cudicini joined Tottenham from Chelsea on a free transfer, and it's this deal which was the last between the two.

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