Manchester City's unbeaten start to the season came to an end as Tottenham secured a 2-1 victory to set up a Carabao Cup quarter-final clash with Manchester United.
Spurs flew out of the traps, and they were ahead as early as the fifth minute when Timo Werner latched onto Dejan Kulusevski's pass before emphatically finishing past Stefan Ortega for his first goal since March 10.
There was a blow for the hosts as a distraught Micky van de Ven left the pitch with a suspected hamstring injury, but it never halted Spurs' momentum.
Pep Guardiola said after the last round that he did not want to "waste energy" on the Carabao Cup and his player were playing like they believed their manager's words. A lacklustre Man City had no answer and Pape Sarr's long-range strike beat Ortega to double the lead in the 25th minute.
City eventually started to grow into the contest and began dominating the ball as Spurs looked to get in at the break with their two-goal advantage. However, Savinho - often the bright spark for City in the opening 45 minutes - delivered a cross to the far post where Matheus Nunes converted to give the visitors a huge lifeline just before the break.
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Injuries plagued the second half with Savinho stretchered off - he was replaced by Jacob Wright with Erling Haaland remaining on the bench - while Spurs had to replace Cristian Romero and Werner as the rhythm of the game was disrupted.
Spurs were a threat on the counter as City pushed for an equaliser, and the visitors had goalkeeper Ortega to thank for two excellent stops to deny Brennan Johnson and Kulusevski.
Spurs' big chance to win the game fell to substitute Richarlison, who was sent through on goal by a wayward Josko Gvardiol throw, but the striker wasted the golden chance by sending a weak effort straight at Ortega.
It was a chance he was almost left to rue but for team-mate Yves Bissouma. The midfielder came up up with a superb block right on the goal line to keep out Nico O'Reilly's last-gasp effort as Spurs kept alive their hopes of a first trophy since 2008.
'A big result for Spurs'
Sky Sports' Jamie Redknapp:
"The game could have gone either way when you think of Bissouma's clearance of the line which was a big moment.
"Man City do punish you because they keep the ball and sometimes you press and it's not on, and they can pop the ball around you and then they are in on your back four.
"Then you lose Van de Ven and then Romero, so Spurs had to suffer, but it was a big result for them.
"No disrespect to Spurs winning, but you could see who wanted it more. When Guardiola isn't brining on Haaland with 15 minutes to go, that tells you were Man City were.
"They already had a couple of injuries and didn't want anymore. With the players City had on the pitch you still felt they could do a job and they did have their chances.
"But for Tottenham, it's a big result. They are in the draw, and they want that trophy."
WATCH: All the goals as Spurs send City crashing out...
'Wins like this can accelerate growth of team'
Spurs boss Ange Postecoglou:
"My last win is always my best win. I continue to see growth in this group of players and this team.
"I want them to have these moments because I know how important it is to accelerate the growth of what we're doing.
"But for me, personally, nothing really changes. It's about trying to continually push this group to become the team we want to be.
"We're not there yet, fair to say. I'm really optimistic and bullish about this group of players. I just think they've got a really high ceiling and we've just got to keep focusing on that."
'We have to keep going and win every game'
Tottenham's Dejan Kulusevski to Sky Sports:
"It is important to win and go through in the cup. When you play a great team like City you always want to win - I am proud of the boys.
"I always love this game, playing the best teams in the world, I want to be one of the best players in the world.
"We have to keep going and win every game. We have to keep focused."
Guardiola: We are in a difficult position
Man City boss Pep Guardiola to Sky Sports:
"Exceptional. The young players did well.
"An incredible top side they are so fast and I am really pleased. We play so good. If you play a game that quick they attack quicker, we played really good. Of course, in the second half there was transitions they could have finished the game - I know perfectly how good we played.
"Football sometimes, we are in a difficult position with the amount of players."
On injuries, Guardiola added: "It is what it is. It is normal. The limit of the players is there.
"We will see tomorrow [on Savinho's injury].
"Jack Grealish and Kyle Walker, no chance to play the next games."
What's coming up for Spurs and Man City?