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Saturday, October 24, 2026

How Tottenham can end their Stamford Bridge hoodoo

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Tottenham Hotspur Football Newsletter

Just as Tottenham thought they were turning a corner, a trip to Stamford Bridge, a place where they have won once in their last 41 attempts, approaches.

It is very much in keeping with Spurs’ luckless streak that, less than a week after recording their first league win of the season, the fixture list has coughed up a trip to high-flying, free-scoring Chelsea.

Against no other team have the Blues won more than against Spurs, and they will relish the opportunity to let their fearsome attacking triumvirate loose on the north Londoners’ patchwork defence.

You will be hard-pressed to find a derby fixture this one-sided, yet Chelsea fans will be wary that all good things must come to an end.

James Maddison celebrates

James Maddison celebrates scoring for Spurs against Coventry

Getty Images

Roberto De Zerbi is waiting in the wings. He knows history is written by the victors, and he is determined to change the narrative around this storied fixture.

“There are many, many negative records, but for me it's one motivation more,” De Zerbi said in his pre-match press conference.

“Yes, it's a derby against one very good team, very good coach, they have a clear style of play, great players, but also Tottenham players are very good.”

Spurs are on the up. They were not at their best against Coventry, but they showed a newfound cutting edge to get over the line and fend off a second-half fightback from Frank Lampard’s side.

Their performances have been better than their results suggest and they have the pace and physicality in wide positions to exploit the spaces between Chelsea’s wing-backs and outside centre-backs.

Xabi Alonso’s side also affords teams time and space on the edge of the box, and that is why De Zerbi will be disappointed that James Maddison, scorer of Spurs’ opening goal against Coventry with a delightful whipped effort, has once again not been able to train fully in the build-up to Saturday’s clash.

Maddison made an impact off the bench as De Zerbi learned firsthand the hold Chelsea have over Spurs in May. The England midfielder’s quick feet and sharp movement nearly led to a late equaliser, but after nearly a year out with an anterior cruciate ligament injury, he was not sharp enough to take advantage.

Conor Gallagher

Getty

Five months on, not much has changed for Maddison. He is still struggling for fitness and is unlikely to start tonight, with De Zerbi once again scrambling for midfield options.

“In the first three days Maddison didn't work with us, I don't know if he's ready for tomorrow,” the manager added. "I don't know if [Maddison and Dejan Kulusevski] will start on the pitch or on the bench but they are both available to play.

“We have to manage both in the best way we can because they are different players, in qualities, in personality in experience, and we need them."

Sandro Tonali could fill the void left by Maddison. His physicality dragged Spurs back into the ascendancy after Coventry’s equaliser, and he hummed around the top of the box with intent, coming close with a couple of efforts that punched a pack but lacked accuracy.

Conor Gallagher, who could stand in for Maddison in the No10 role, also has an eye for a third-man run and would surely love to get one against his former club.

Chelsea are equal parts brilliant and brittle, and if Spurs match their intensity, they can startle a team that have already shipped 13 goals this term and will place their faith in 21-year-old goalkeeper Mike Penders after first-choice shot-stopper Emiliano Martinez suffered a fractured jaw against Everton last weekend.

Spurs are beginning to look like a team, and while expectations are low that they will get a result against Chelsea, they are quietly building an identity under De Zerbi.

Fast starts and three-at-the-back, Chelsea and Spurs are more similar than they would like to admit. It might be 17th vs 4th, but derbies are rarely contested on the form book alone.

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