AC Milan sail into quarter-finals after goalless draw against Tottenham

Tottenham’s UEFA Champions League campaign came to an end after failing to overturn a 1-0 deficit in the last 16 against AC Milan.

Antonio Conte returned to the touchline following gallbladder surgery but his tactics and substitutions were loudly questioned by disgruntled home supporters on an infamous night in the club’s modern history.

Stefano Pioli’s Milan didn’t have to do too much in order to see off the supposed threat of Spurs and advanced to the quarter-finals of this competition for the first time since they won it in 2007.

The visitors were the first team to have a real half-sight of goal. A cleverly-worked free-kick saw Sandro Tonali slip in Junior Messias, who ghosted past Ben Davies easily with a quick side-step, but he dragged his shot across the face of goal.

The closest Tottenham came to an opener in the first half was when a deflected low cross from Harry Kane bounced wide off the shins of goalkeeper Mike Maignan.

Just after the break, Milan again went close to breaking the deadlock when Brahim Diaz stumbled his way deep into the box and got a shot away, but he was too close to Fraser Forster and his effort was denied.

Pedro Porro’s introduction from the bench sparked some life into Spurs, providing more dynamism down the right flank, but they still struggled to carve out chances.

The clunky Pierre-Emile Hojbjerg, similarly to Diaz, managed to fall over his own feet dribbling into the area, forcing Maignan into a save high at his near post.

A snap-shot from Olivier Giroud was palmed away in similar vein by Forster as Milan sought to hit a panicking Tottenham on the counter, while a diving Kane header from a Porro cross bounced off the turf and behind.

With under 15 minutes remaining, Cristian Romero picked up a second yellow charge for a high challenge on Theo Hernandez, all but killing the tie.

Home fans loudly booed Conte’s decision to replace forward Dejan Kulusevski with defender Davinson Sanchez with the hosts still needing a goal in the final 10 minutes.

Deep into six minutes of stoppage time, Kane headed a free-kick from Son down at Maignan, who did well to palm it away with haste, before Divock Origi went down the other end and hit the post.

That was the last piece of goal-mouth action as Spurs’ exit was sealed.