Seven-time winners AC Milan reached the Champions League quarter-finals for the first time in 11 years as a disciplined display earned them a drab 0-0 draw at Tottenham Hotspur on Wednesday and a 1-0 aggregate victory.
On a freezing night in north London the Italians comfortably protected the slender advantage they established in the first leg of their last-16 tie at the San Siro as Tottenham huffed and puffed to little effect and exited with a whimper.
Tottenham failed to muster an attempt on target in the first half as their frustration boiled over with manager Antonio Conte booked for letting his emotions get the better of him while they had defender Cristian Romero sent off late on.
Milan could have made it a more comfortable night had they taken any of the good chances they created but in the end a masterclass of game management saw them through.
While Stefano Pioli's Milan can look forward with optimism, Tottenham's season is fizzling out after a dismal week in which they also lost in the FA Cup to second-tier Sheffield United and to Wolverhampton Wanderers in the Premier League.
Milan may be some way off returning to their European pomp but while they lack the household names of the late 1980s and early 1990s, Pioli's team had too much craft for a meek Tottenham side who were booed at the final whistle.
"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," Pioli said. "We made it to the quarters, now let's see what happens in the draw."
THIRD GEAR
The match kicked off 10 minutes late because of traffic issues and in truth Tottenham never got out of third gear.
Considering it was flagged as their biggest game of the season there was a mystifying lack of urgency from the hosts in the first half in which they offered the home faithful nothing to warm their spirits.
Tottenham's three-man attack of Harry Kane, Son Heung-min and Dejan Kulusevski were forced to feed on scraps and while Milan were hardly any more potent they did have the first decent chance when Junior Messias drilled a shot wide.
The Italians came close to taking the lead just after the interval when the ball broke for first-leg scorer Brahim Diaz but his shot was blocked by the legs of Fraser Forster.
With the clock showing 64 minutes Tottenham finally warmed the gloves of Milan keeper Mike Maignan as Pierre-Emile Hojbjerg, suspended for the first leg, fired in an angled drive that was parried over for a corner.
As Tottenham committed men forward gaps appeared at the back and Rafael Leao had an effort blocked and then sent another attempt over the crossbar.
Kane sent a stooping header wide as the game began to open up and Tottenham rolled the dice by sending on forward Richarlison in place of wing back Emerson.
Conte was then jeered for hauling off Kulusevski for defender Davinson Sanchez as time ran out.
Kane went close to levelling in stoppage time with a skidding header superbly saved by Maignan but Milan almost crowned their night on the counter-attack with substitute Divock Origi hitting the post in front of their already-celebrating fans.
Choup-Moting powers Bayern
Bayern Munich forward Eric-Maxim Choupo-Moting scored against his former club and Serge Gnabry added a late second as the Germans beat Paris St Germain 2-0 on Wednesday to reach the Champions League quarter-finals.
The 33-year-old Choupo-Moting, who played for PSG from 2018-20, tapped in from Leon Goretzka's assist in the 61st minute and substitute Gnabry struck in the 89th minute to seal the hosts' 3-0 aggregate win after a 1-0 victory in Paris.
The Germans made sure of their last-eight spot after shutting out PSG superstars Lionel Messi and Kylian Mbappe and are one of the title favourites going into the last eight.
"In the first half, we didn't do what we had talked about before very well," Bayern coach Julian Nagelsmann said. "There was too much space.
"But we defended better in the second half and were dangerous on the ball. In the end, we deserved to win."
"If we show maximum hunger with emotion and we couple that with our quality then we can achieve anything."
PSG's long wait to win Europe's premier club trophy for the first time goes on.
Without injured forward Neymar, the French team were sharper in the early stages and went close through Mbappe and a double effort from Messi in the 25th minute.
Bayern gradually took control, however, and had a chance when Jamal Musiala's 32nd-minute shot was blocked by keeper Gianluigi Donnarumma.
Despite PSG captain Marquinhos being taken off with a rib injury in the 36th minute, the visitors almost went ahead when under-pressure Bayern keeper Yann Sommer lost possession in the box.
"We did not manage to score when we were on top of things," PSG coach Christophe Galtier said.
"Then we concede a ridiculous goal. What made the difference is the fact we missed some key players in both legs. It's a big disappointment but we have to swallow it."
The quarter-final draw will take place on March 17.
