AC Milan will take a slender one-goal advantage to North London in their Champions League last 16 tie with Tottenham Hotspur after beating the English side 1-0 at San Siro this evening.
An early goal from Brahim Diaz was enough to separate the sides as Antonio Conte suffered defeat back in his homeland.
It is yet another disappointing result for Spurs after their humbling 4-1 defeat to Leicester City in the Premier League at the weekend.
After a four-game losing run which saw them defeated twice by rivals Inter Milan as well as shipping nine goals to Lazio and Sassuolo, Milan have now won back-to-back games for the first time since the World Cup break.
Conte had a selection headache in his Spurs midfield following the injury picked up by Rodrigo Bentancur at the weekend.
Pierre-Emile Hojbjerg was already out suspended and Yves Bissouma has been nursing an ankle injury, so Pape Matar Sarr and Oliver Skipp partnered each other in midfield for just the second time.
Pedro Porro also dropped to the bench after his difficult debut at the King Power Stadium on Saturday at right wing-back.
It was down Tottenham's right-hand side where they fell behind early on too as excellent, strong play from Theo Hernandez eventually led to Brahim's opener.
After beating Christian Romero in the air, Hernandez drove into the area and forced a save from Fraser Forster who then quickly got up to make a miraculous second stop from Brahim, but the Spaniard was on hand to nod home on the goal line at the third time of asking.
Hernandez continued to be a menace to the Spurs defence, and especially Romero who had a torrid night and was also slightly fortunate to not see red for a high challenge on Sandro Tonali.
It was a half of few chances, as cheap fouls and injury stoppages interrupted much of the play.
Spurs did very little and their only remotely threatening moment came when Harry Kane hit the crossbar before Son Heung-min was flagged offside in the build-up.
The visitors appeared content to keep the scoreline down to just one, but were very fortunate when Milan missed two golden opportunities around the 75 minute mark.
Charles De Ketelaere's first touch, just seconds after coming on, saw him miss a brilliant chance to open his account for the Rossoneri but he got it all wrong and skewed his header well off target.
The Belgian attacker has now failed to find the net in his first 26 games in a Milan shirt after his move from Club Brugge in the summer.
Just moments later, another header resulted in another glaring miss, this time from defender Malick Thiaw who was culpable of wasting a great chance.
A fabulous ball from Leao into the six-yard box gave Thiaw a simple task, but he was also unable to keep his effort on target.
That is how it finished though as Spurs failed to muster any chances despite six minutes of additional time, with Milan coming out victorious by one goal to nil.
Spurs have some huge domestic fixtures to prepare for before the second leg in early March, including back-to-back London derbies versus West Ham United and Chelsea next.
After falling out of the Serie A top four recently, Stefano Pioli's side will take the short trip to Monza at the weekend as they look to have their season back on track.
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