Tottenham moved up to fifth in the Premier League after goals from debutant Steven Bergwijn and Heung-Min Son secured a 2-0 win over Manchester City.
Pep Guardiola's side failed to score and also missed a penalty on their only other visit to the Tottenham Hotspur Stadium last April and history repeated itself as Ilkay Gundogan's first-half miss from 12 yards proved costly.
- Tottenham 2-0 Man City - Match report and highlights
- Premier League Table | Fixtures | Top scorers
- Is this Guardiola's biggest ever challenge?
City remain 22 points behind Liverpool in second place with the season's objectives now in limbo; no chance of retaining their title and yet unlikely to be caught in the runners-up position.
Sky Sports' Ben Grounds and Gerard Brand assess the key performers after Jose Mourinho secured only his sixth win as a manager over Guardiola in the great battle of football's two great masterminds.
Tottenham
Hugo Lloris - 8
A massive difference to the Tottenham side. Got a crucial couple of studs on Sergio Aguero's shot to deflect it onto the post and came to Tottenham's rescue to keep out Ilkay Gundogan's 40th-minute penalty. A commanding presence who claimed well to deny Gabriel Jesus a late consolation late on.
Toby Alderweireld - 7
The Belgian centre-half contributed to Aguero striking the woodwork as he slid across to narrow the angle. Alderweireld was then back on his line to thwart the Argentine once more after Lloris had clashed into Japhet Tanganga. Booked.
Davinson Sanchez - 7
Was a very relieved man after a sloppy pass out from the back allowed Riyad Mahrez to set up Aguero for the strike that Lloris brilliantly kept out. For the first time under Pep Guardiola, City suffered back-to-back goalless games, and Sanchez played his part, making a game-high 10 clearances, including one off his own crossbar in the final seconds!
Serge Aurier - 6
Typically bombed down the right as per Jose Mourinho's instructions. Suffered a rush of blood to the head when challenging Aguero inside the box - given after a VAR review - but Lloris spared his blushes with a fine save to keep out Gundogan's penalty. Recovered and grew in confidence.
Japhet Tanganga - 6
Another tough assignment on only his third Premier League start. City looked to target the Tottenham left side with Kevin De Bruyne and Mahrez seeing plenty of the ball. The youngster suffered a mix-up with Lloris shortly after the restart which very nearly led to Gundogan atoning for his penalty miss. Stood up to the challenge well.
Harry Winks - 7
A happy 24th birthday for Winks, who sparked Spurs' second-half resurgence by drawing the foul which led to Oleksandr Zinchenko's red card. It was Winks' fourth successive Premier League start - his longest run under Mourinho - and he repaid the faith shown in him with another mature display in Tottenham's engine room.
Giovani Lo Celso - 7
A fifth successive start for Lo Celso and first since making his move from Real Betis permanent last week. It looks a shrewd piece of business. Christian Eriksen's presence at the club had lingered like a dark cloud, but that has now been lifted by his departure and the emergence of the 23-year-old as a ready-made replacement. Booked.
Steven Bergwijn - 8
A thrilling moment for the player at his new club. One touch on the chest and bang. The Dutchman covered his face during his celebration, but there was no mistaking the identity of the goalscorer. Mourinho was set to make a change soon after the Zinchenko dismissal but Bergwijn changed that with one magical, wand of a strike. Suffered cramp and departed soon after.
Heung-Min Son - 7
Had looked isolated during the opening hour as long balls seeking the South Korean kept coming back towards the Spurs goal. But having looked isolated, he burst into life and took his goal very well albeit via a deflection off Fernandinho.
Lucas Moura - 8
Tottenham's best player when this game was a contest. Showed great composure to set up Bergwijn and caused countless problems for Kyle Walker with his direct running as part of Tottenham's fluid front three. Moved through the middle after Dele Alli's substitution to keep City guessing.
Dele Alli - 6
In the absence of Harry Kane, Alli was deployed as the false number nine, but Spurs failed to register a shot on target in the opening 45 minutes. Alli ran himself into the ground, but there were very few encouraging signs that this is a position to which he will want to return. Replaced with 20 minutes remaining.
Subs
Tanguy Ndombele - 6
Looked like he had a point to prove when he replaced Alli, passing with real purpose into Son's feet as Spurs duly doubled their lead within a minute of him coming on.
Erik Lamela - 6
Came on for the tiring Bergwijn and helped to double up with Aurier to ensure Sterling was kept subdued as City's attempts to set up a frantic finale never got off the ground.
Eric Dier - n/a
Replaced Moura for the final six minutes to sit in front of the defence and ensure only a third clean sheet in 18 games since Mourinho's arrival.
Man City
Ederson - 5
Dwelled as he rushed out of goal early on, nearly allowing Lucas Moura in, but didn't face his first shot until the 63rd minute, Spurs' opener. Not much he could have done about either goal.
- Find out more about Sky Sports
- Live football on Sky Sports this week
- Sky VIP - thousands of prizes including Premier League tickets
Kyle Walker - 5
Hit and miss. Caught in two minds whether to support Mahrez or fulfill defensive duties. Booked.
Nicolas Otamendi - 5
Good on the ball and gets City out from the back at pace, but still a weak link positionally. Was slightly out of position for Spurs' second, committing to allow Son space in-behind.
Fernandinho - 6
Started superbly, but fell away. City, without a favoured central defender, are cutting their nose off to spite their face, with Fernandinho sorely missed in midfield.
Oleksandr Zinchenko - 4
Needlessly involved in the first-half scuffle after the VAR chaos, and then silly to barge Winks for the second yellow. Even if Winks looked for it, Zinchenko should be nowhere near him.
Rodri - 6
Anchored the midfield well enough defensively, without being spectacular. Struggled to move the ball at pace to stretch Spurs, who played narrow. Booked.
Ilkay Gundogan - 5
Missed a penalty and a glorious chance just after the break on the stretch. Did make the most passes for City in the opposition half.
Kevin De Bruyne - 6
A calm head amid the chaos for City, and happy to go one step back before going two forward. Got into good positions, but needed those around him to be more clinical on the ball.
Riyad Mahrez - 7
A constant menace, and a first touch to die for. On his game, Mahrez is one of the most enjoyable City players to watch, and was unlucky to be on the losing side.
Raheem Sterling - 6
Better, but still missing that killer instinct in the box. Still without a goal or assist in nine games. Booked.
Sergio Aguero - 5
Should have scored at close range after the VAR chaos just before the break, but was unlucky not to open the scoring before that as Lloris touched his low shot onto the post.
Subs
Joao Cancelo (on 64) - 5
Brought on for Aguero in an attempt to shore up the defence after Spurs' opener, and didn't do much wrong.
Gabriel Jesus (on 72) - 5
Dotted between the centre-backs in an attempt to make an opening, but didn't have long enough to make an impact.
Bernardo Silva - n/a
Played through the centre after replacing Sterling but with six minutes left, had very little time to make an impact.