AC Milan booked a place in the Champions League quarter-finals after holding a depleted Tottenham at bay following a goalless draw in the second leg of Wednesday’s round-of-16 at the Tottenham Hotspur Stadium.
Trailing 1-0 from the first leg in Italy, Tottenham offered precious little to suggest the tie could be turned around despite manager Antonio Conte back on the sidelines after recovering from gallbladder surgery.
Their hopes were fueled as the home side tried to build some momentum late on, but with 12 minutes remaining, defender Cristian Romero was shown a second yellow card to leave them with 10 men.
Spurs have now failed to score in their last three matches, losing two, in which they have been knocked out of the FA Cup and Champions League, as well as their Premier League top-four hopes have suffered a blow.
Milan, who are in a similar battle to get back into the Champions League next season, have reached the last eight of Europe’s premier competition for the first time since 2011-12.
Despite trailing from the first leg, Tottenham showed little urgency in the first half as they went to half-time without a goal for the seventh time in their eight Champions League games this season.
Indeed, with Milan completely comfortable and Spurs lacking ideas and intensity in possession, neither side had a shot on target in the first 45 minutes.
The only true moment of danger before the break came from a Milan free-kick routine on 18 minutes, which saw Junior Messias free on the right side of the box, only for the wing-back to scuff his shot well.
And it was the visitors who finally got the first try on goal six minutes into the second half.
The only goalscorer in the first leg, Brahim Díaz, managed to get past a defender after Messias’ cutback, but Fraser Foster, deputizing for the injured Hugo Lloris in the Tottenham goal, was able to get down and block with his capable Feet.
Tottenham finally began to show some urgency as the game ticked into its final quarter and Pierre-Emile Hojbjerg first called Mike Megnon into action, forcing the Milan goalkeeper to curl a shot over the bar.
But a harsh challenge from Romero on Theo Hernandez near the touchline produced a deserved second yellow and seemed to be the end of Tottenham’s lame challenge.
The home fans’ frustration was evident when Conte was booed for replacing Dejan Kulusevski with defender Davinson Sanchez as time ran out.
There was late drama in second-half stoppage time when a Harry Kane header forced a fine save from Meganson before Divock Origi fired a breakaway effort against the post at the other end.
But it was too little too late for Tottenham, leaving Milan to go into the quarter-final draw on 17 March.