AC Milan ended their long wait for a place in the last eight of the UEFA Champions League after a 0-0 draw with Tottenham confirmed a 1-0 aggregate success.
The Rossoneri looked the more likely side to extend their aggregate advantage in a cagey opening half, Junior Messias spurning two opportunities.
The 31-year-old dragged his low effort across the face of goal after a well-worked free-kick routine, before blasting a left-footed strike high into the crowd after cutting in from the left following good work by Rafael Leão.
The hosts managed to get themselves into promising positions in the first 45 minutes, but were ultimately unable to pick out their attackers in the opposition box.
Milan began brightest after the restart too and almost doubled their lead across the tie when first-leg match-winner Brahim Díaz burst into the box but Fraser Forster was alert to the shot at his near post.
It took until after the hour for Antonio Conte’s men to force Mike Maignan into meaningful action, the French international acrobatically tipping over Pierre-Emile Højbjerg’s fierce shot.
The match gradually opened up and former Arsenal striker Olivier Giroud hooked straight at Forster from close range, while home captain Harry Kane was unable to steer a stooping header on target just moments later.
Tottenham looked to step up a gear in the closing stages, but their task was made tougher when Cristian Romero was dismissed with just under 15 minutes remaining for a second bookable offence.
There was a flurry of activity in added time as both sides pressed for a late winner, Kane’s powerful header pushed away by Maignan. Milan broke immediately and substitute Divock Origi clipped the inside of the upright from the edge of the box, though it mattered not in the end.
Reaction
Stefano Pioli, Milan coach, speaking to Prime Video: “We knew it would be tough, but we managed. I asked the players to show character. We never gave up, and we deserved to progress. We need to think step by step. We made it to the quarters, now let’s see what happens in the draw.”
Olivier Giroud, Milan forward, speaking to Prime Video: “We made it to the last 16 and [now] we deserved this result, even though we could have scored more. We showed quality, spirit, and we could have won tonight as well. It’s a great result. I told the players that we deserved to be in the Champions League and we wanted to do well in it.”
Antonio Conte, Tottenham coach: “I don’t think we played with too much patience in the first half. Our objective was to attack them from the start, to press them high. Milan, however, did well against our pressing. I cannot say much to my lads because in terms of commitment they gave everything they had.”
Discussion about this post