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. Son Heung-min's brace cancelled out the opener from Sterling, but the forward restored City's lead after Bernardo Silva's fortunate equaliser.
Aguero's brilliant strike then 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.
|Inter 2 Empoli 1: Keita, Nainggolan secure Champions League berth in thriller|
|SPAL 2 AC Milan 3: Kessie brace not enough for Champions League place|
|Lyon star Aouar eager for Guardiola link-up|
|Seven-try St Helens thrash Castleford Tigers|
|Donnarumma injured in AC Milan´s final Serie A fixture|
|Relaxed ´outsider´ Federer cruises through, Paris woe for Cecchinato|
|Juventus deny making an approach for Guardiola|
|De Ligt keeping options open amid Barca and Man United rumours|
|Sampdoria 2 Juventus 0: Allegri suffers late defeat in final game|
|Wiesberger fends off MacIntyre to win Made in Denmark|
|Sokratis: Arsenal boss Emery the best coach of my career|
|Verstappen: I gave it my all to pass Hamilton|
|Cataldo takes stage win on rough day for Roglic|
|Kovac reassured as Hoeness recommends Boateng for Bayern exit|
|I was fighting with the spirit of Lauda - Hamilton wins his ´hardest race´|
|Galatasaray leading race to sign Babel|
|Ireland flanker O´Brien ruled out of Rugby World Cup|
|Fittler hopeful on Frizell as wounded Dragons send duo for scans|
|Hamilton clings on for Monaco glory but Mercedes´ one-two run ends|
|Federer enjoys serene Roland Garros return|
|Suarez hits out at questions over Barcelona commitment|
|Injured Auger-Aliassime withdraws from French Open|
|Sancho ´guaranteed´ to stay at Borussia Dortmund|
|Kerber stunned by teenager Potapova in Roland Garros opener|
|This party is for everyone! Emotional Parejo leads Valencia in Copa celebrations|
|Cleary in for New South Wales, Maloney misses out|
|Emery had to convince Arsenal stars to care about Europa League|
|Frizell suffers Origin scare, Addo-Carr at the double for Storm|
|Leonard´s experience made a difference, admits Antetokounmpo|
|Pochettino fears Kane call could decide Champions League final|
|Giannis: This is just the start for the Bucks|
|Best player in the NBA? Leonard focused on Raptors´ success|
|Manchester United 2 Bayern Munich 1 (1998-99) - Where are they 20 years on?|
|Manchester United 1998-99: The best wins of Ferguson´s treble from Turin to Barcelona|
|Yankees sweep double-header, remain atop AL East|
|Tuchel´s PSG extension - Opta numbers help to explain new deal|
|Herring beats Ito to claim WBO super-featherweight title|
|Three takeaways from Raptors´ historic win over Bucks|
|Raptors defeat Bucks to earn first ever Finals berth|
|MLS Review: Rooney salvages draw for DC, Union beaten|
|Liverpool want to emulate Man City dominance – Henderson|
|Marcelino revels in ´happiest day´ after Copa del Rey success|
|Kovac praises Bayern turnaround after completing double|
|Red Sox´s Devers robbed of home run by Minute Maid Park girder|
|Warriors´ Iguodala considering retirement|
|Na leads at Colonial, Spieth two shots back|
|Valverde vows to fight on at Barcelona|
|I can be one of the best in the world - Zverev defiant after return to winning ways|
|Finland to face Canada in final after downing Russia|
|Valverde not to blame for Barcelona´s Copa defeat, says president Bartomeu|
|Rummenigge reaffirms Bayern Munich´s Kovac stance after DFB-Pokal triumph|
|Barcelona season bittersweet after Copa loss, says Pique|
|Ribery proud after making victorious Bayern Munich farewell|
|Centurion Smith unfazed by England boos|
|Warrington battle past Wigan as Giants humiliate Hull|
|Barcelona 1 Valencia 2: Valverde pressure increases as Catalans denied historic Copa win|
|Leinster retain Pro14 title to spoil Hogg farewell|
|F1 Raceweek: Hamilton hopes rain will not scupper likely Monaco glory|
|Bayern Munich 3 RB Leipzig 0: Lewandowski´s brace helps secure domestic double|
|Crusaders march on as Sharks enjoy derby delight|
|Champions League failure would be ´huge disappointment´ for Atalanta - Gasperini|
|Lennon offered full-time Celtic job after treble-treble|
|Paris Saint-Germain must pull together in one direction to improve - Tuchel|
|Toulon end Castres´ reign, La Rochelle and Montpellier seal play-off spots|
|Coutinho, Semedo & Arthur start Copa del Rey final after injury problems|
|Yastremska shrugs off Garcia to claim maiden clay title|
|Gasly handed Monaco grid penalty|
|Without him, I would have one title – Hamilton dedicates Monaco pole to Lauda|
|Neymar, Mbappe and how to help Kimpembe: Tuchel´s Paris Saint-Germain to-do list|
|Outgoing Ribery and Robben on Bayern bench as Neuer starts DFB-Pokal final|