Three transfers Chelsea stole from Tottenham as Xavi Simons hijack could now land major payback
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Jack Heath
Thu 28 August 2025 18:08, UK
Tottenham are plotting to get their own back at Chelsea by hijacking their deal for Xavi Simons after the Blues burnt Spurs on three separate occasions.
The Blues have been on the hunt for the Dutch attacking-midfielder for a large portion of the summer with Chelsea looking to accelerate a deal for Simons after the possible sale of Christopher Nkunku.
Yet, in what could be a major change of events, Tottenham are reportedly expected to pounce on Enzo Maresca’s target with an “officially” submitted offer of €70million [£61m] (Florian Plettenberg).
This could be a moment of redemption for the Lilywhites after many occasions of being hijacked by their London rival which has followed the club round for years like a bad odour.
Possibly on the verge of finally getting some well-deserved payback, Football Insider looks at three of the most notable times Chelsea stole Spurs targets from right under their noses.
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Back when Tottenham were under the reign of Andre Villas-Boas and Gareth Bale was the name on everyone’s lips, the club were pushing to reach new heights and bring in more quality players.
The former Blues boss was set on bringing in Brazilian wonderkid Oscar from Internacional, dubbed “one of the most exciting talents to emerge from Brazil in years”, according to The Daily Mail.
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The Lilywhites submitted an offer between the region of £11m-18m to land the then 20-year-old and bring him to north London.
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However, the then-Champions League holders Chelsea raised the bar by submitting a whopping £25m which, unsurprisingly stopped Daniel Levy going any higher.
The South American was a definite “Spursy” player and would’ve fit in nicely at White Hart Lane.
Shame the chairman and ownership refused to break the piggy bank as per usual.
As a Spurs fan, this is one of those transfers that will forever give me a reason to dislike the Blues after they outmanoeuvred us at the last moment with a deal seemingly all but confirmed.
The Lilywhites fought off Liverpool to become front runners for a move for Willian from Anzhi Makhachkala for a reported deal of £30m (The Guardian).
The winger had even completed a medical at White Hart Lane with an announcement looking like it would be a matter of hours away.
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Then, in dramatic fashion, owner Roman Abramovich finessed the deal by speaking to Willian’s agent and submitting an increased offer of £32m, sending the Brazilian on his way to Stamford Bridge.
Levy was reportedly “incandescent” with the hijack with both the chairman and then Chelsea owner in a bitter spat over transfer vendettas.
Manager of the time Jose Mourinho memorably stated that Spurs should have done the medical “in secret”, as the Lilywhites lost out yet again to their rivals, with the winger proving a thorn in Tottenham’s side on the pitch frequently in the subsequent years.
In the same window as Oscar, the west London side also stole another Spurs target out from underneath them.
Eden Hazard had spoken to former Tottenham boss Harry Redknapp about joining him at White Hart Lane to replace Real Madrid bound Luka Modric.
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The Belgian caught the eye of the Lilywhites, Manchester United and Manchester City before eventually landing on a move to Stamford Bridge for £32m (The Daily Mail).
The former Madrid starlet said that he was “tempted” by the prospect of playing in north London but when the club failed to qualify for the Champions League he was put off.
Conversely, the Blues, having won the European competition at the end of the 2011-12 campaign, won him over in another bitter blow for Levy and co.
Hazard, of course, went on to be one of the best players the Premier League has ever seen on West London, only increasing the disappointment.