Seven-time winners AC Milan reached the Champions League quarter-finals for the first time in 11 years as a disciplined display earned them a 0-0 draw at Tottenham Hotspur and a 1-0 aggregate victory.
On a freezing night in north London the Italians comfortably protected the slender advantage they established in the first leg of their last-16 tie at the San Siro as Tottenham huffed and puffed to little effect.
Tottenham failed to muster an attempt on target in the first half as their frustration boiled over with manager Antonio Conte booked for letting his emotions get the better of him while they had defender Cristian Romero sent off late on.
Milan could have made it a more comfortable night had they taken any of the good chances they created but in the end a masterclass of defensive game management saw them through.
While Stefano Pioli’s Milan can look forward with optimism, Tottenham’s season is fizzling out after a dismal week in which they also lost in the FA Cup to second-tier Sheffield United and to Wolverhampton Wanderers in the Premier League.
Milan may be some way off returning to their European pomp but while they lack the household names of the late 1980s and early 1990s, Pioli’s team had too much craft for a Tottenham side who were booed at the final whistle.
The match kicked off 10 minutes late because of traffic issues and in truth Tottenham never got out of third gear.
Considering it was flagged as their biggest game of the season there was a mystifying lack of urgency from the hosts in the first half in which the home fans were given nothing to warm the spirits on a bitter cold night.
Tottenham’s three-man attack of Harry Kane, Son Heung-min and Dejan Kulusevski were forced to feed on scraps and while Milan were hardly any more potent they did have the first decent chance when Junior Messias drilled a shot wide.
The Italians came close to taking the lead just after the interval when the ball broke for first-leg scorer Brahim Diaz but his shot was blocked by the legs of Fraser Forster.
With the clock showing 64 minutes Tottenham finally warmed the gloves of Milan keeper Mike Maignan as Pierre-Emile Hojbjerg, who was suspended for the first leg, fired in an angled drive that was parried over for a corner.
As Tottenham began to commit men forward gaps appeared at the back and Rafael Leao had an effort blocked and then sent another attempt over the crossbar.
Kane sent a stooping header wide as the game began to open up and Tottenham rolled the dice by sending on forward Richarlison in place of wing back Emerson.
Conte was then jeered for hauling off Kulusevski for defender Davinson Sanchez as time ran out.
Kane almost levelled in stoppage time with a header superbly saved by Maignan but Milan could have crowned their night on the counter-attack with substitute Divock Origi hitting the post.