AC Milan took a step towards their first Champions League quarter-final appearance for 11 years as Brahim Diaz's goal gave the Italians a 1-0 win over Tottenham Hotspur in their last-16 first leg at the San Siro on Tuesday.
The Spaniard headed in a rebound in the seventh minute after a superb double save by Tottenham's second-choice keeper Fraser Forster and the seven-time winners kept the Londoners at bay.
Spurs, weakened by injuries and suspensions, responded positively in the first half to dominate possession but were unable to seriously worry the hosts.
Milan should have increased their advantage after the break with substitute Charles De Ketelaere and defender Malick Thiaw wasting glorious headed chances.
Tottenham sent on Brazil forward Richarlison for the last 20 minutes and, while they were unable to avoid a first-ever defeat by Milan, they will head home still hopeful of turning the tie around and reaching the last eight.
"It wasn't hard to prepare this game tactically, with all the duels, but I am very happy with how my players performed," Milan coach Stefano Pioli said.
"We could have scored a second goal -- we had some clear chances. I am happy with the performance but it's only the first leg and the next game will be surely more difficult."
Milan's record against Premier League clubs has been lamentable in recent years with only one win in 17 ahead of their clash with Antonio Conte's Spurs side.
But faced with inconsistent opponents who were without the suspended Pierre-Emile Hojbjerg and injured Rodrigo Bentancur in midfield and sidelined goalkeeper Hugo Lloris, Milan deservedly ended that run with a tenacious display.
The San Siro crowd did not have to wait long to have something to cheer as Theo Hernandez got the better of Cristian Romero before powering a shot at Forster who saved well.
Diaz's rebound effort was also brilliantly saved but he reacted quickly to bundle in a header.
With 22-year-old Oliver Skipp and Pape Sarr, 20, in central midfield, Tottenham did gain a foothold and Son Heung-min's free kick was met with a glancing header by Eric Dier but it went straight at Milan keeper Ciprian Tatarusanu.
Tatarusanu then saved well from Son with Harry Kane hitting the rebound against the crossbar, although a goal would have been disallowed anyway for offside.
Spurs huffed and puffed after the break without much reward and were fortunate that Milan did not give themselves a bigger cushion for the second leg in March.
In the space of a couple of minutes De Ketelaere headed wide after Olivier Giroud nodded the ball back across goal and then Tottenham got another let-off as Thiaw also missed the target with an equally inviting chance.
Dier, who will be suspended for the second leg after picking up a booking, should have done better with a chance at the other end but Spurs could have few complaints about the final score.
"I expect another tough match in the return leg. We should have done better for their goal, then it was a battle in front of a difficult atmosphere," Conte said.
"Let's not forget, Milan won the league last year -- we didn't."
