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Tottenham Hotspur ended their six-game winless run in the Premier League by beating Coventry City 3-1. James Maddison was one of the stars of his side’s first league win this season.
James Maddison was handed his first Spurs start after nearly 18 months, and he marked his return to the starting lineup in some style. With 14 minutes on the clock, the creative midfielder curled a spectacular goal past the hapless Carl Rushworth to open the scoring for Tottenham against Coventry City. Omar Marmoush and Ben Davies scored later to seal the deal.
The England international has been working hard to attain full fitness from an ACL injury that he suffered last August. He has had bumps on the road to recovery but stayed focused and finally was handed a starting berth in the Tottenham side by Roberto De Zerbi.
Addressing the press conference on Friday, De Zerbi gave an injury update on his Tottenham squad ahead of the trip to Chelsea. He claimed that Maddison missed the first three days of training this week and is unsure whether he will be ready for Saturday’s derby.
“In the first three days, Maddison didn’t work with us. I don’t know if he is available for tomorrow. We can play with Tel, with Marmoush, with Gallagher,” De Zerbi said (h/t Football London).
The game against Coventry also marked Dejan Kulusevski’s first appearance for the club in more than 500 days. The Swede came on as a second-half substitute to help Spurs see off the game.
Dejan Kulusevski’s situation is also not clear, having not fully trained after returning to action. He has been on an individual training programme in the initial days, and De Zerbi stressed he does not want to take unnecessary risks with players given the amount of injuries he has in his squad.
James Maddison and Dejan Kulusevski provided two of the biggest moments in Tottenham’s 3–1 victory over Coventry on Monday night.
— Gary Ward (@GaryRWard) October 23, 2026
Roberto De Zerbi has updated fans on both players ahead of Tottenham's visit to Chelsea on Saturday. https://t.co/CYvUJXXKPi
“Like I said many times, I don’t want to take risk because if you analyse this period of European football, you can see many, many injuries and not for Tottenham but everyone,” he added.
“Kulusevski worked well but in the first days stayed individual.”
Both Maddison and Kulusevski’s fitness must be carefully managed. The creative midfielders have come back from serious knee injuries and cannot be risked. If the duo are ruled out, De Zerbi will have to rely on Conor Gallagher to bring creativity to his side against his former employers.