He AC Milan advanced to the quarterfinals of the Champions League after drawing goalless with 10 players from Tottenham on Wednesday.
the goal of Brahim Diaz in the first leg of the round of 16 was enough to separate the teams, as even the return of manager Antonio Conte failed to inspire a comeback for the spurs.
Seven-time European champions Milan topped the match at the Tottenham Hotspur Stadium, which saw Christian Romero sent off in the second half.
Harry Kane’s 94th-minute header was the closest the home side had come to leveling the score on aggregate, before Milan substitute Divock Origi hit the post in a frenzy finish.
Conte returned to the bench for Tottenham after spending two and a half weeks in Turin recovering from gallbladder surgery.
But he could only watch as his team failed to defeat Italian champions Milan, meaning Tottenham’s 15-year wait for a trophy continues.
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