Milan secured a spot in the Champions League quarter-finals for the first time in 11 years with a goalless draw against Tottenham on Wednesday, preserving their 1-0 lead from the first leg.

Brahim Diaz’s early goal in the first leg gave Milan a crucial advantage, which they defended stoically at Tottenham Hotspur Stadium. Both teams struggled to create chances in a game devoid of much-attacking flair, with neither team managing to test the opposition goalkeeper in the first half.

In the second half, Tottenham showed more urgency but still lacked the quality to break down Milan’s defence. Stand-in goalkeeper Fraser Forster kept out Diaz’s shot with his feet, while Milan’s Mike Maignan dealt comfortably with Pierre-Emile Hojbjerg’s angled drive.

Tottenham’s hopes were further dented when Cristian Romero was sent off for a second bookable offense, but Harry Kane came close to forcing extra time with a superb header that Maignan saved.

However, there was no late drama, and the match ended goalless. Divock Origi went closest to breaking the deadlock with a late breakaway attack that hit the post, but Milan held on to their aggregate lead.

Tottenham fans booed their team off at half-time after the team failed to find a way through Milan’s defence. The team’s exit from the Champions League comes just a week after they were knocked out of the FA Cup.

The match was delayed due to traffic congestion around the stadium, but neither team was able to find their rhythm in the first half. Emerson’s deflected shot was the best chance of the half, but it failed to test Maignan.

Milan’s solid defence proved too difficult for Tottenham to penetrate, as they advanced to the quarter-finals of the Champions League.