Milan held Tottenham to a 0-0 draw on Wednesday to preserve their 1-0 lead from the first leg and advance to the Champions League quarter-finals for the first time in 11 years.
Brahim Diaz’s goal in the early stages of the reverse fixture gave Milan something to protect at Tottenham Hotspur Stadium and they did exactly that in a game of few chances.
Neither side managed an attempt on target in the first half and, while Spurs did show more urgency in the second period, there was not enough quality to break down Milan.
Spurs, who had Cristian Romero sent off 11 minutes from time for a second bookable offence, have now exited the Champions League and FA Cup in the past week.
Kick-off was delayed due to traffic congestion around the stadium and neither side truly turned up in the first half.
The onus was on Tottenham to find a goal but Emerson’s deflected shot, which failed to test Mike Maignan, was the best they could muster and they were booed off at half-time.
Stand-in Spurs goalkeeper Fraser Forster was called into action early in the second period when keeping out Diaz’s shot with his feet.
Maignan was finally required with 63 minutes played, but Pierre-Emile Hojbjerg’s angled drive was simple enough to deal with.
Romero flew into a challenge on Theo Hernandez to receive a second booking, yet Harry Kane so nearly salvaged extra time when his header was superbly kept out by Maignan.
There was to be no late drama, though, with Divock Origi going closest to making the breakthrough on the day when hitting the post at the end of a late breakaway attack.