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Tottenham must break eight-year Chelsea curse and Roberto De Zerbi may just know how

The Tottenham boss may need to repeat his Brighton & Hove Albion trick on Saturday when his side take on Chelsea

Roberto De Zerbi and Xabi Alonso embrace

Roberto De Zerbi and Xabi Alonso embrace ahead of the pre-season fixture between Tottenham and Chelsea (Photo by Darren Walsh/Chelsea FC via Getty Images)

Roberto De Zerbi will be hoping his Tottenham Hotspur side can kick on following their first victory of the season against Coventry City on Monday night.

The 3-1 victory, which saw James Maddison, Omar Marmoush and Ben Davies get on the scoresheet, moved Tottenham up to 16th in the Premier League and would have given everyone in the squad a boost. The return of Dejan Kulusevski, plus the impressive performance of Maddison, were also real highlights and De Zerbi has called on his players to keep improving.

"I hope we can play with this attitude, with this mentality, with this union, and improving at the same time, improving confidence, improving everything we need," De Zerbi said after the win against Frank Lampard's side.

"We have to play better because we can play better. I think other games, even if we play with different opponents, it would be easier as a tactical game. But for sure, now we have to push in this way."

Before the next international break in November, Tottenham face Chelsea at Stamford Bridge on Saturday (October 24), Crystal Palace in north London on October 31 and Leeds United at Elland Road on November 7. It could be a vital block of fixtures if De Zerbi wants to get Spurs' season back on track.

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Xabi Alonso's Chelsea team will be a real test, however. The Blues are currently fourth in the league and go into the clash having won 2-0 at Everton. They have won four of their seven league games so far this season, scoring 17 goals in the progress, although they have also conceded 13.

With the likes of Morgan Rogers, Cole Palmer and Joao Pedro showcasing their talents, De Zerbi will know how difficult Saturday will be. Tottenham's record at Stamford Bridge does not make for good reading, either.

Roberto De Zerbi, manager of Tottenham Hotspur looks on during the Premier League 2026/27 match between Tottenham Hotspur and Coventry City at Tottenham Hotspur Stadium on October 19, 2026 in London, England

Roberto De Zerbi during Tottenham Hotspur's win over Coventry City.(Image: Photo by Harry Murphy - Danehouse/Getty Images)

In fact, the last time Tottenham recorded a win at Chelsea's home ground was in April 2018. Christian Eriksen and Dele Alli (two) were both on the scoresheet that day as Mauricio Pochettino masterminded a huge victory over Antonio Conte.

Since that day more than eight years ago, Tottenham have failed to win any of their 10 visits to Stamford Bridge. The Lilywhites have lost their last six games against Chelsea in the Premier League and have not left Stamford Bridge with a point since the 2-2 draw in August 2022.

De Zerbi has actually faced Chelsea six times already in his career (five with Brighton and once with Tottenham last season) and boasts a record of two wins and four loses. While the record does not make for sensational reading, the Italian at least does know how to beat the Blues at Stamford Bridge, having done so with Brighton in April 2023 as goals from Danny Welbeck and Julio Enciso ensured a 2-1 victory.

Additionally, Tottenham and Chelsea also locked horns in a pre-season friendly this summer. In what was just Alonso's second game in charge, Richarlison, who, ironically, has since been exiled from the Spurs squad, scored a stoppage-time winner at the Accor Stadium in Sydney to give De Zerbi perhaps another boost over Chelsea and Alonso.

De Zerbi will be hoping he can use this all to his advantage as he bids to break the eight-year Tottenham curse and earn a victory at Stamford Bridge on Saturday.

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