AC Milan secured a spot in the Champions League quarterfinals after holding a lackustre Tottenham at bay to go through 1-0 on aggregate following a goalless draw in Wednesday’s round-of-16 second leg at Tottenham Hotspur Stadium.
Trailing 1-0 from the first leg in Italy, Tottenham offered precious little to suggest they could turn the tie around, despite having manager Antonio Conte back on the sideline following his recovery from gallbladder surgery.
As the home side tried to build some momentum late on, their hopes were all but ended with 12 minutes remaining when 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 games, losing two, in which they have crashed out of the FA Cup and Champions League as well as seeing their Premier League top-four hopes suffer a blow.
Milan, who are in a similar battle to make it back to 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 displayed little urgency in the first half as they reached half-time without scoring for the seventh time in their eight Champions League games this season.
Indeed, with Milan wholly comfortable and Spurs lacking ideas and intensity in possession, neither side managed even a shot on target in the first 45 minutes.
The only true moment of danger before the break came from a rehearsed Milan free-kick routine on 18 minutes that got Junior Messias free down the right of the box only for the wing-back to scuff his shot well wide.
And it was the visitors who finally had the first effort on goal six minutes into the second half.
The scorer of the only goal in the first leg, Brahim Diaz, managed to bundle past a defender after Messias’ cutback but Fraser Forster, continuing to deputize for the injured Hugo Lloris in the Tottenham goal, was able to get down and block with his legs.
Tottenham finally began to show some urgency as the game ticked into its final quarter and Pierre-Emile Hojbjerg called Mike Maignan into action for the first time, forcing the Milan goalkeeper to tip a shot over the bar.
But a rash challenge from Romero on Theo Hernandez near the touchline produced a deserved second yellow and seemingly the end of Tottenham’s limp 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 deep into second-half stoppage time when a Harry Kane header forced a fine save from Maignan before substitute Divock Origi dinked a breakaway effort against the post at the other end.
But it was all too little too late for Tottenham, leaving Milan to go into the quarterfinal draw on March 17.