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Timo Werner’s first goal in 18 matches helped Tottenham knock Manchester City out of the Carabao Cup with a 2-1 win after a pulsating fourth-round tie.
Werner set Spurs on course for victory when he rifled home in the fifth minute, which was followed by a superb curled strike from Pape Sarr midway through the first half.
City responded with a Matheus Nunes goal on the stroke of half-time but after Pep Guardiola decided against bringing on Erling Haaland, Tottenham held on for a crucial win which sent them into the quarter-finals and helped push them a step closer to ending a 16-year trophy drought.
It was not a solely positive night for Ange Postecoglou after he lost Micky van de Ven to injury and City winger Savinho left the pitch on a stretcher as the packed fixture schedule hit home for both managers.
Guardiola had stated last month that City would not waste any energy on this competition, but named a stronger than expected team with only two inexperienced younger players included in Nico O’Reilly and James McAtee.
It was a similar story for Postecoglou, although one of the five players he recalled after the 1-0 loss at Crystal Palace immediately justified his selection.
Werner returned in place of 17-year-old Mikey Moore and ended his goal drought which stretched back to March early on.
Spurs played out from the back impressively before Archie Gray found Brennan Johnson, who flicked into the path of Dejan Kulusevski and he produced a perfectly-weighted cross for Werner to slam home from 14 yards.
Tottenham’s momentum was checked when Van de Ven felt his hamstring after a tackle on Savinho and looked distraught as he walked off to be replaced by Destiny Udogie.
After City youngster O’Reilly needed treatment soon after, the hosts almost grabbed a second from a short corner but Kulusevski ballooned his effort over.
It should have been a warning sign for the visitors, but it was not heeded and Spurs made it 2-0 through Sarr in the 25th minute.
Werner and Kulusevski combined from a short corner before the latter rolled into the path of Sarr, who produced a sublime curled effort from 25 yards that beat Stefan Ortega and nestled into the bottom corner.
City produced a response with a free-kick from Ilkay Gundogan sent over before a dangerous Nunes cross evaded Phil Foden.
The chances kept on coming with a Savinho effort curled wide and Foden directed another free-kick off target before the deficit was reduced.
Savinho got to the byline and crossed in for Nunes to side-foot home at the back post in the fourth minute of first-half stoppage time.
Guardiola followed up the goal with the introduction of Josko Gvardiol and Mateo Kovacic at half-time.
Postecoglou also brought on Yves Bissouma before he made the surprise decision to replace stand-in-captain Cristian Romero, who had been excellent.
Tottenham could have restored their two-goal advantage by this point after Werner raced half the length of the pitch only to fire inches wide not long after Johnson tested Ortega with a stinging effort.
Ortega was required again when Johnson played in Kulusevski, but his low strike was pushed out before the injury curse struck again.
Firstly, Savinho went down – moments after Bernardo Silva had been brought on – and had to leave on a stretcher, which was soon followed by Werner being forced to limp out of the action.
The next opportunity went to City, but substitute Jacob Wright curled wide with 21 minutes left before Guardiola turned to Jahmai Simpson-Pusey, which meant Haaland would not be introduced.
Haaland-less City still pushed for a leveller and almost forced penalties in the 89th minute when Guglielmo Vicario failed to claim a corner, but O’Reilly’s shot on the turn was brilliantly booted wide by Bissouma on the line to hand the visitors a first defeat of the season.
