AC Milan progressed to the quarter-finals of the Champions League for the first time since 2012 as the Italian champions held out for a 0-0 draw at 10-man Tottenham to win 1-0 on aggregate.
A European elimination hot on the heels of an exit from the FA Cup means Tottenham’s 15-year wait to win a trophy will extend for at least another season.
Antonio Conte’s return to the touchline failed to inspire a response from his side as Tottenham were toothless in attack and had to play the final 12 minutes a man down as Cristian Romero was sent off for two bookable offences.
Kick-off was delayed by 10 minutes after the later arrival of both sides due to traffic congestion, but it took far longer for the contest to get going.
Conte was back in charge after taking more time after the first leg to recover from gallbladder surgery.
The Italian was his usual animated self and was shown a yellow card by referee Clement Turpin for his protestations at a booking for Clement Lenglet.
However, his players lacked the same energy as Spurs failed to rise to the occasion.
Milan produced the one piece of imagination befitting of a Champions League knockout tie before the break as a well-worked free-kick found Junior Messias, but the Brazilian dragged his shot wide.
Spurs had lost four of their previous six games, including defeat to second-tier Sheffield United in the FA Cup.
The home support could not hide their frustration as the half-time whistle was met with a smattering of boos.
Conte was unable to provoke a response at the break as Spurs needed stand-in goalkeeper Fraser Forster to keep them in the tie.
Brahim Diaz scored the only goal of the first leg and his jinking run inside the Spurs box just lacked the finish as Forster’s outstretched leg deflected the ball to safety.
Spurs at least forced Mike Maignan into a save 25 minutes from time as he tipped over Pierre-Emile Hojbjerg’s strike.
Conte gambled by switching to a front four for the final 20 minutes with Richarlison joining Harry Kane, Dejan Kulusevski and Son Heung-min up front.
But there was still precious little service for Kane and hope of a Tottenham fightback disappeared with Romero.
The Argentine often treads a fine line with his discipline and saw red for the third time in his Spurs career after lunging in on Theo Hernandez.
Kane came closest to an equaliser when his header from a Son free-kick was well saved by Maignan low to his right in stoppage time.
Milan should have made sure of victory on the night as well as on aggregate but Sandro Tonali wasted another glorious chance by going for goal himself with teammates in support before Divock Origi’s effort came back off the inside of the post.
But it did not matter as the seven-time European champions held firm to end more than a decade of waiting to reach the last eight.