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 on Wednesday 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.
The subdued hosts were not helped by having defender Cristian Romero sent off for a second yellow card in the 78th minute.
Milan could have made it a more comfortable night had they taken a few 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.
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