Omar Marmoush scored his first goal for Tottenham as Roberto De Zerbi's men battled to a 3-1 win over Coventry City.
Spurs had gone winless in their first six Premier League matches this term, and another failure to take all three points on Monday would have seen them draw to within one game of matching their longest winless start to a season in the competition.
Yet Marmoush's superb finish and Ben Davies' stoppage-time effort saw Spurs get over the line at Tottenham Hotspur Stadium.
James Maddison, making his first competitive start for Spurs since May 2025, opened the scoring in the 14th minute.
The former Coventry playmaker met Mohammed Kudus' cutback on the cusp of the visitors' area and bent a sensational strike into the top-left corner.
Yet Spurs failed to build on their lead, with Dominic Solanke having a goal disallowed for offside before he arrowed over, and Coventry were level early in the second half when the in-form Jack Rudoni hammered in from close range.
Sandro Tonali blazed over as Spurs got straight onto the front foot, though, and that pressure paid off as Marmoush spun Milan van Ewijk, who took an elbow to the face for his troubles, and curled beyond Carl Rushworth, who might have done better.
Rushworth should definitely have kept out the decisive third in the 96th minute, but Coventry's goalkeeper allowed Davies' tame shot to sneak in and settle the contest.
Three points in N17! https://t.co/lACSKpyNam
— Tottenham Hotspur (@SpursOfficial) October 19, 2026
Long-awaited victory comes with long-awaited Kulusevski return
It was a big night for two Tottenham stars who have had a torrid time of it over the past year or so.
Maddison made his first start in a meaningful game for Spurs since a Europa League semi-final tie against Bodo/Glimt at the end of the 2024-25 campaign, with the midfielder having missed the majority of last season due to a serious knee injury.
He had at least returned towards the end of the campaign, but the same could not be said for Dejan Kulusevski, who was back in a Premier League matchday squad for the first time in 526 days.
Kulusevski came on to huge applause in the 87th minute, and though he was clearly rusty, every touch and pass the Swede made was cheered by the home crowd, who will be thrilled to have him back and will now be praying he is over his injury issues.
Spurs only created chances worth a combined 0.87 expected goals, but they became the first team to score three goals from outside the box in a Premier League game since Fulham against Leicester City in May 2023.
Since the start of 2024-25, Tottenham have dropped more points from winning positions in Premier League home games than any other side (30), so the nerves will certainly have crept in, especially given Spurs' dismal home record.
Yet they got the job done in the end, and De Zerbi will now be hoping Spurs, who moved above Coventry and into 16th place, can kick on. Next up for them is a trip to Chelsea on Saturday.