Tottenham reached the Champions League semi-finals for the first time in their history with an exhilarating 4-4 away-goals win over Manchester City on a remarkable night at the Etihad.

Raheem Sterling was denied a dramatic winner in stoppage time when Sergio Aguero was ruled offside in the build-up after a VAR check, as Fernando Llorente’s unorthodox finish – which also survived a VAR check for handball – with 17 minutes remaining ensured Mauricio Pochettino’s side face Ajax for a place in the final.

Sterling (4, 21) and Heung-Min Son (7, 10) both scored twice during a frantic first-half which also saw Bernardo Silva immediately cancel out the South Korean’s second strike (11).

Aguero then blasted home at the near post (59) to put City ahead in the tie, but Llorente’s effort from Kieran Trippier’s corner was awarded as Spurs ended City’s hopes of a quadruple in the most extraordinary fashion.

Spurs, who last reached the European Cup semi-finals in 1962 where they were defeated by Benfica, saw their first-leg advantage wiped out inside four minutes.

City had won 12 matches on the trot at the Etihad, and they made the perfect start as Sterling collected Kevin De Bruyne’s pass before cutting inside Trippier and finding Hugo Lloris’ bottom corner.

But Son showed his freshness to turn the tie back in Tottenham’s favour with two goals in the blink of an eye. The South Korean benefited from a slack clearance by Aymeric Laporte in cutting out Dele Alli’s through-ball to steer his first-time shot under the legs of Ederson.

City had barely had the chance to compose themselves when Laporte compounded his error as Lucas Moura pounced on his heavy touch to spark a swift counter-attack and Son punished Kyle Walker for allowing him too much space to curl in his second.

Immediately from kick-off, Aguero found Bernardo Silva on the right, and with Danny Rose isolated, the midfielder managed to squeeze his shot past Lloris at his near post via a deflection off the England left-back.

This was already the four fastest goals at the start of any Champions League game – and City weren’t finished in a frenzied first half as four goals in 11 minutes became five in 21 – meaning the hosts only needed one more goal to hold the upper hand.

Their third was a thing of beauty, as Bernardo turned provider, driving at pace from midfield before finding De Bruyne on the right, and with Trippier switching off at the far post, Sterling was found exquisitely by the Belgian to finish from a tight angle.

Son came close to completing his hat-trick before the interval when his left-footed shot whistled past Ederson’s post from the angle, and the forward was booked moments after the restart for a foul on De Bruyne which rules him out of the first leg of the Champions League semi-final.

Lloris kept out Sterling from point-blank range after David Silva’s cut-back before Rose prevented Bernardo Silva from sliding in the rebound. Lloris produced an even better save to keep out De Bruyne’s drive as City continued to lay siege on the Tottenham goal.

Llorente would have the final say, however, as Trippier’s corner was met at the front post by the Spaniard’s hip, and despite referee Cuneyt Cakir checking VAR for a suspected handball, the goal stood.

There was still time for more gripping, late drama as Sterling thought he had completed his hat-trick from Aguero’s cross – but replays showed the Argentine had strayed offside before collecting Bernardo Silva’s deflected pass as the Spurs players raised themselves from their haunches to celebrate the most breath-taking of victories in defeat.