Raheem Sterling was denied by VAR in injury time as Manchester City's quadruple hopes came to an end in the most dramatic of circumstances against Tottenham in a classic Champions League quarter-final tie.
The England international thought he had a hat-trick at the death at the Etihad Stadium, but a review showed Sergio Aguero was offside in the build-up as Tottenham progressed via the away goals rule despite losing 4-3 on the night.
Spurs had already been assisted by VAR when Fernando Llorente bundled in from close range 17 minutes from time, which made it 4-4 on aggregate and ultimately booked a semi-final date with Ajax.
A chaotic first half had City 3-2 up at the break, as Sterling wiped out Son Heung-min's brace then scored the hosts' third following a fortunate Bernardo Silva equaliser.
Aguero's brilliant strike had seemingly put City into the semis before VAR deemed Llorente's apparent handball to be accidental and Pep Guardiola's men saw wild celebrations for Sterling's last-gasp effort curtailed in sensational scenes.
A rip-roaring start astonishingly produced four goals in the first 11 minutes, with City initially overturning Spurs' first-leg lead through Sterling's gorgeous curling finish just inside the area.
But Spurs soon had the lead on the day – Son's effort from the edge of the box inexplicably finding its way past Ederson after an Aymeric Laporte error to level, before the Spurs star had another with a fierce strike into the top-right corner following another mistake from City's French centre-back.
Despite those lapses, City were in an obstinate mood and equalised barely a minute later when Silva's close-range effort deflected in off Danny Rose.
An incisive move in the 21st minute put City ahead on the night, as Sterling met Kevin De Bruyne's exquisite low cross and converted at the back post.
Aguero seemed to have ended Spurs' resistance in the 59th minute when latching on to a De Bruyne pass and finishing emphatically inside the near post.
But it was not enough, as Kieran Trippier's corner struck Llorente, the ball appearing to hit his elbow and thigh on its way in.
Sterling thought he had sent City through in the final seconds of stoppage-time, finishing from the middle of the box, but VAR spotted Aguero straying offside to bring a swift end to the jubilant scenes, securing Spurs' passage after a remarkable encounter.
What does it mean? Immortality out of reach for City
So much of the talk around City in recent weeks has revolved around a potential quadruple, with Guardiola's men previously looking almost unbeatable in every competition.
However, once again the Champions League will elude City, with Spurs' positive approach paying dividends, as at no point did they look intent on coming to the Etihad Stadium and sitting on their 1-0 lead.
De Bruyne on another level
It may not be much of a consolation to City given the outcome of the tie, but De Bruyne was back to his very best on Wednesday. The midfielder drove forward with purpose, supplied three assists and would have got a goal were it not for a fine Lloris save in the second half.
Laporte errors punished
In a game with so many goals, defenders were unlikely to stand out for the right reasons. Laporte was the most culpable, with his errors leading directly to Spurs' first two goals, before then not doing enough to get in front of Llorente for what proved to be the decisive goal in the tie.
Key Opta Facts:
- Tottenham have reached the semi-finals of the Champions League/European Cup for the second time in their history, also doing so in 1961-62 under Bill Nicholson.
- Spurs are the seventh English side to reach the Champions League semi-finals (also Man Utd, Man City, Liverpool, Chelsea, Arsenal and Leeds) – England are now the nation with the most unique semi-finalists (overtaking Spain).
- Five goals were scored in the opening 21 minutes of this game – it is the shortest amount of time it has ever taken for five goals to be scored in a Champions League match.
- No side has been knocked out at the Champions League quarter-final stage by English teams on more occasions than Manchester City (twice; also in 2017-18 vs Liverpool).
- Manchester City winger Raheem Sterling has been directly involved in 26 goals (19 goals and seven assists) in 20 games in all competitions at the Etihad this season, more than any team-mate.
These two do it all over again on Saturday, with Spurs this time hoping to derail City's Premier League title charge at the Etihad Stadium.