Steven Bergwijn marked his debut with a superb volley as Tottenham won a bad-tempered Premier League affair with 10-man Manchester City to boost their top-four hopes.
The result lifts Spurs to fifth, four points behind fourth-placed Chelsea, while City remain second, 22 points behind leaders Liverpool who can win the title on 21 March when they play Crystal Palace.
The 22-year-old’s goal came with Spurs’ first shot on target, after Oleksandr Zinchenko had been dismissed for a second yellow card and City midfielder Ilkay Gundogan had seen a first-half penalty saved by Hugo Lloris.
Son Heung-min’s effort, which deflected off Fernandinho as it flew past City goalkeeper Ederson into the bottom left corner confirmed a valuable victory for the hosts.
Football Daily podcast: Bergwijn’s brilliant debut and tough times at the bottom
Pep Guardiola’s City side had arrived in London chasing their fifth league win in six games and dominated possession but failed to convert a glut of glorious chances.
Lloris brilliantly flicked a Sergio Aguero effort on to the post and the Argentine was then at the centre of a chaotic few minutes towards the end of the first half, winning a penalty awarded by VAR following Serge Aurier’s clumsy challenge.
Gundogan however, saw his spot-kick – which took four minutes to be given – saved by Spurs keeper Lloris, with VAR then asked to rule on whether the France goalkeeper had fouled City’s Raheem Sterling as both pursued the rebound.
Tottenham’s Toby Alderweireld and Zinchenko were booked as both sets of players confronted each other in the aftermath, while Spurs boss Jose Mourinho appeared angered at the referee’s failure to book Sterling for diving when a second penalty was not awarded.
Sterling had earlier appeared fortunate to escape with only a 12th-minute booking, after replays showed his studs landing on the ankle and lower shin of Spurs midfielder Dele Alli.
City though were reduced to 10 men after the break, with Ukrainian Zinchenko receiving his marching orders for a foul on Harry Winks.
That allowed Spurs to gain a foothold in the game, with Bergwijn firing Lucas Moura’s clever cross into the bottom right corner from 15 yards to set them on their way.
Until the hour mark this had looked like being another occasion on which Spurs were going to sorely miss Harry Kane as the focal point of their attack.
Son and Moura provided dynamism and debutant Bergwijn showed some neat touches, but Kane’s ability to hold the ball and bring others into play was absent as the hosts repelled wave after wave of City attacks.
And then the game dramatically swung in Tottenham’s favour, thanks largely to Winks’ surge forward which drew Zinchenko into a rash challenge and hastened his early departure.
City, who had been readying Gabriel Jesus, were suddenly forced into a rethink and while they attempted to reorganise Spurs went ahead.
Bergwijn, who arrived at the club on Wednesday in a £27m deal from PSV Eindhoven had last scored on 7 December against Fortuna Sittard.
But there was nothing routine about the way he introduced himself to supporters of the north London club – capping a tenacious display with a fine goal.
It marked a dream debut for the Netherlands winger, who pulled up with cramp in the second half, but who was afforded a hero’s ovation when he was withdrawn after 70 minutes.
While Spurs manager Mourinho cut a frustrated figure in the first period over perceived injustices, the roles were reversed after the break with his old nemesis Guardiola appearing exasperated by his own team.
Having reminded his City side to be “more clinical” after their Manchester derby loss on Wednesday, he appeared agitated by their first-half penalty miss and the decision not to award them a second penalty.
And that was compounded two minutes into the second period when German midfielder Gundogan missed a gilt-edged chance, firing over from six yards after Sterling had laid the ball into his path and Aguero’s initial effort was cleared off the line by Alderweireld.
The champions had 18 shots but only hit the target five times and both substitute Jesus and Bernardo Silva were unable to convert late chances.
City’s lack of cutting edge ensured a sixth defeat of the season, which is as many as in their past two title-winning campaigns combined.