AC Milan's Champions League credentials were barely tested by Tottenham as the seven-time winners advanced to the quarterfinals.
The Italian champions, however, still have a chance of winning club football's biggest prize for the first time since 2007, while Spurs' 15-year wait for a trophy goes on.
A goalless draw against 10-man Tottenham on Wednesday was enough to secure a 1-0 aggregate win in the round of 16, with Brahim Diaz' first-leg strike decisive.
Even the return of manager Antonio Conte could not inspire a comeback from the London club, whose best chance came in the 94th minute when Harry Kane's header was pushed away from the line by Milan goalkeeper Mike Maignan.
Milan were allowed to cruise through the game at the Tottenham Hotspur Stadium, which saw Cristian Romero sent off in the second half.
Kane's effort was the closest the home team came to levelling 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 Italian manager could only watch on as his team failed to break down Milan, meaning Spurs are still waiting for a first major piece of silverware since winning the League Cup in 2008.
Tottenham are now left to battle for a place in the Premier League top four, which would provide a route back into the Champions League. Conte's future will also be the subject of scrutiny amid ongoing speculation about whether he will remain at the club beyond the end of the season.
Milan, meanwhile, can dream of an eighth title in Europe's elite club competition.
Only Real Madrid, with 14 titles, have been crowned European champions on more occasions than Milan.
Few expect Stefano Pioli's team to break its drought in the competition 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 barely troubled Milan in the first half.
A deflected cross from Kane that 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 Hjbjerg was then denied by Maignan after a driving run in the box.
Spurs 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.
