Spurs and Chelsea to do business for the second time in 17 years with double deal close

London rivals Tottenham Hotspur and Chelsea are set to do transfer business with one another for just the second time since 2009, it has been reported - with a shock double deal on the cards.

Spurs have spent nearly £400 million during the summer transfer window, having backed manager Roberto De Zerbi to conduct a rebuild of the squad following last season's 17th-placed finish.

That rebuild was expected to conclude with the signing of Everton winger Iliman Ndiaye for a fee of £60 million, with a deal reportedly agreed in principle on Sunday.

Richarlison was due to move the other way in what has been claimed to be a separate deal, but the Brazilian hasn't agreed personal terms over a prospective £35 million move to Everton - and has released an unprecedented statement over the situation on social media.

READ MORE: Richarlison's cryptic message on social media is going viral after Everton deal agreed

Manchester City have now agreed a deal to sign Ndiaye and he is expected to complete the move before the transfer window closes at 11pm on Tuesday.

Spurs have therefore been forced to turn their attentions elsewhere - and are set to sign two players from their bitter London rivals.

Spurs close in on unprecedented double deal with Chelsea

BBC Sport reported on Monday evening that they had entered talks over a loan deal to sign Chelsea winger Mykhailo Mudryk, who is free to leave Stamford Bridge on a temporary basis.

Mudryk was permitted to return to football last month, having been suspended since he failed a drugs test in December 2024. The Ukrainian was banned for four years but his appeal to the Court of Arbitration was 'resolved'.

The FA stated that a change to World Anti-Doping Agency (WADA) procedures since the failed test meant that, had the sample been collected today, the concentration of the banned substance meldonium would not have been reported and he would not have broken any anti-doping rules.

Mykhailo Mudryk is set to leave Chelsea on loan (Image: Getty)

Prior to his £88 million move to Chelsea in January 2023, De Zerbi managed Mudryk at Shakhtar Donetsk and appears keen to reunite with the 25-year-old in north London.

But that is not the only business that is likely to be completed between Spurs and Chelsea.

The Athletic have reported on Monday evening that Spurs had reached an agreement over a surprise move to sign centre-back Tosin Adarabioyo on a permanent basis.

The 28-year-old defender had been made surplus to requirements at Stamford Bridge following the arrival of Maxence Lacroix from Crystal Palace.

It is reported that Spurs have agreed personal terms with Tosin and he will undergo a medical on Tuesday.

He is set to become the fifth centre-back to be discarded by Chelsea this summer, after Trevoh Chalobah joined Como on a permanent deal and Benoit Badiashile, Mamadou Sarr and Axel Disasi all left on loan.

The last time Spurs and Chelsea dealt with each other directly was in 2023, when young striker Jude Soonsup-Bell moved to Spurs to join their development squad.

You have to go back to 2009 for the last time a first team player moved between the two clubs. Goalkeeper Carlo Cudicini was allowed to join Spurs on a free transfer during the winter transfer window, and played 37 games in all competitions over the next four years before departing for LA Galaxy in 2013.