Ange Postecoglou's quest to end Tottenham's trophy drought continued as victory over Manchester City booked a Carabao Cup quarter-final with Manchester United.

The Spurs boss claimed recently he always wins silverware in his second season - and remained on course to fulfil his promise after an entertaining, eventful encounter.

Timo Werner, who had a mixed evening, scored his first goal of the season with an emphatic finish after five minutes, before Pape Sarr doubled the home advantage 20 minutes later with a superb low right-foot finish from 25 yards.

Spurs, though, suffered a setback when they lost key defender Micky van de Ven with a hamstring injury in the 14th minute, and City setting up a tense second half when Matheus Nunes pulled one back in the fourth minute of first-half added time.

City keeper Stefan Ortega kept his side in the contest with fine saves from Brennan Johnson, Dejan Kulusevki and Richarlison, while Werner fired wide when clean through before limping off with a groin muscle injury.

City, who suffered a casualty of their own when the lively Savinho was taken off on a stretcher, almost snatched a late leveller, but Yves Bissouma made a superb block on the line from Nico O'Reilly's effort.

Spurs, without a trophy since their 2008 win in this competition, will be delighted to have bounced back from the weekend's disappointing Premier League loss at Crystal Palace with such a significant win.

They will now host another Manchester side in United, with the game taking place in the week commencing 16 December.

Bitter-sweet night for Werner but joy for Spurs

Werner's night started with delight but still ended with disappointment, despite playing a big part in a hugely important win for Spurs and manager Postecoglou.

The German striker's endeavour and attitude are beyond question, making him a popular figure, but wayward finishing has become his trademark throughout a chequered career.

Werner showed his positive side when he hammered home Kulusevski's pass to give Spurs the ideal start – although the chant of "Timo Werner – he scores when he wants" from the home fans was heavily laced with good-natured irony.

The other side of him was shown when he was clean through on goal, with time to think and steady himself, but shot wide with only Ortega to beat. Limping off before the end through injury compounded his frustration.

In the end, though, Werner's contribution was vital as this unpredictable Spurs team deservedly edged out league champions City, who may have left Erling Haaland on the bench but still had plenty of quality.

There was one large cloud on the home side's night with a first-half injury to Dutch defender Van de Ven, who looked distressed as he went off, clutching his hamstring after a characteristic show of pace chasing back to challenge Savinho.

Postecoglou and Spurs, though, rightly took the acclaim from their delighted supporters as their outstanding record against City at the Tottenham Hotspur Stadium continued with their sixth win in eight games here.

Man City suffer first loss and rare unhappy night

Manchester City manager Pep Guardiola rested some key players for this tie, including master striker Haaland, but there was still enough talent and experience in his team to challenge Spurs.

And when Nunes dragged City back into the game with a composed close-range finish from Savinho's cross, after Spurs had established that 2-0 lead, the stage looked set for a grandstand second half - and Haaland lying in wait should Guardiola require him.

The Norwegian frontman remained on the bench and it was Spurs who created the clearer openings instead.

City came closest two minutes from time when teenager O'Reilly was denied by a priceless goalline clearance from home substitute Bissouma.

Guardiola will be disappointed City have lost their first match of the season, but will be concerned too by injuries to defender Manuel Akanji, who pulled out before kick-off having been named in the starting line-up, and his replacement Ruben Dias also going off at half-time.

And there was another setback when the excellent, dangerous Savinho had to leave the pitch on a stretcher after pulling up injured.

All in all, not one of Manchester City's happier nights.