Tottenham beat Wolves in a shootout to reach the Carabao Cup fourth round after blowing a two-goal lead in normal time.
Goals from Leander Dendoncker and Daniel Podence cancelled out earlier efforts from Tanguy Ndombele and Harry Kane to take the game to penalties.
But Ruben Neves, Dendoncker and Conor Coady all missed in the shootout as Bryan Gil's penalty proved decisive for Tottenham.
Spurs travel to Burnley next.
French midfielder Ndombele broke into the box and turned defender Willy Boly to open the scoring at Molineux, before captain Kane made it 2-0 on 23 minutes for Spurs after being played though by Dele Alli.
Belgium midfielder Dendoncker headed in Rayan Ait-Nouri's corner before the break and then set up Podence to equalise.
Goalkeeper John Ruddy kept Wolves in the game, denying Kane twice with superb blocks on the line to take the match to spot-kicks.
With the scores level at 2-2 in the shootout, Neves blasted over. Italian keeper Pierluigi Gollini, playing only his second game for Spurs, saved from Dendoncker after Gil had converted.
Wolves' fate was then sealed when Coady hit the bar.
There was bad news too for the Midlands side when defender Yerson Mosquero was taken off on a stretcher in the fifth minute of his debut.
Wolves boss Bruno Lage: "It is hard to lose this game because of the way we prepared.
"The way we are creating chances and the way we are playing are the positive things from this game. But the way we are conceding chances and goals from the opposition makes me very disappointed.
Tottenham boss Nuno Espirito Santo on Kane: "He has much more to give and it's about the game, improving and growing together.
"In terms of the squad and preparation we have players who have 65/70 sessions and we have players who have 15 sessions.
"Until we have been able to balance everything, then it will be the moment when the players will improve."
"We spent a lot of time preparing [for penalties] because it's not luck. It's having a goalkeeper who has the right info, the players taking the responsibility."