LONDON (AP) — AC Milan advanced to the quarterfinals of the Champions League after holding 10-man Tottenham to a goalless draw on Wednesday.

Brahim Diaz' strike in the first leg of the round-of-16 matchup was enough to separate the teams as even the return of manager Antonio Conte could not inspire a comeback from Spurs.

Seven-time European champions Milan cruised through the game at the Tottenham Hotspur Stadium, which saw Cristian Romero sent off in the second half.

Harry Kane's 94th minute header was the closest the home team came to leveling the score on aggregate — before Milan substitute Divock Origi hit the post in a frantic finish.

Conte was back on the sideline for Tottenham after spending two-and-a-half weeks in Turin recovering from gallbladder surgery.

But the he could only watch on as his team failed to break down Italian champions Milan, meaning Spurs’ 15-year wait for a trophy goes on, having failed to win any silverware since the League Cup in 2008.

Tottenham is now left to battle for a place in the Premier League top four, which would provide a route back into the Champions League.

Milan, meanwhile, can dream of an eighth title in Europe's elite club competition.

Only Real Madrid has been crowned European champion on more occasions than Milan, which last won club soccer’s biggest prize in 2007.

Few expect Stefano Pioli’s team to break that drought this season, but it heads into the last eight after a defensively resolute performance subdued a Tottenham attack that was short of ideas.

While the finish was thrilling, the rest of the game had provided few chances for either side.

Tottenham had gone into the game on the back of bruising losses to second-division Sheffield United in the FA Cup and Wolverhampton in the Premier League.

While Conte’s return should have provided a boost, there was little sign of it as Spurs allowed Milan to cruise through the first half.

A deflected cross from Kane that Milan goalkeeper Mike Maignan had to block at his near post was the home team’s best chance before the break.

Conte had let his own frustrations boil over when receiving a yellow card for remonstrating a booking for Clement Lenglet in the first half, shortly after Romero had received his first caution.

Tottenham’s intensity improved in the second half, but Diaz threatened to extend Milan’s lead when forcing Fraser Forster to save with his legs shortly after the restart.

Pierre-Emile Højbjerg was then denied by Maignan after a driving run in the box.

Spurs continued struggled to create chances and their task was made even more difficult when Romero fouled Theo Hernandez and was sent off for a second yellow card in the 78th.

With just one goal separating the teams there was always the chance of late drama.

Kane came close to providing it with his powerful header that Maignan pushed off the line.

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The Associated Press