Tottenham have it all to do in the second leg, with AC Milan taking a 1-0 advantage to London, thanks to an early goal from former Manchester City player, Brahim Diaz.
Diaz gave Milan an early lead, heading into an empty net after his initial effort was saved brilliantly by Fraser Forster. Cristian Romero was beaten too easily to the ball by Theo Hernandez in the build-up.
Tottenham struggled to create any clear-cut opportunities. Eric Dier came closest for Spurs, with a mistimed header, when the defender wriggled free from a corner.
AC Milan could have taken a bigger advantage to London, with Charles De Ketalaere and Malick Thiaw missing brilliant opportunities, both putting headers past the post.
Tottenham host AC Milan in the second leg on Wednesday, March 8, as Spurs look to come from behind to progress to the Champions League quarter-finals.
AC Milan
Ciprian Tatarusanu – 7/10
Good stop to deny Son, the flag was up, but the Romanian did not know that. Did not have much to do.
Pierre Kalulu – 7/10
Solid throughout. Rarely put a foot wrong and, on the whole, he managed to frustrate Heung-min Son.
Simon Kjaer – 6/10
Did not contend with Kane well. The usually commanding centre-back was beaten by the striker and struggled to deal with Kane’s hold-up play.
Malick Thiaw – 8/10
Four tackles and one interception in an emphatic first-half performance, leaving Dejan Kulusevski frustrated on the right. Missed a brilliant opportunity to double Milan’s advantage after he headed wide of the left post.
Theo Hernandez – 8/10
Played almost as a left-winger and was the furthest man forward at times. Good effort to force Cristian Romero into a mistake which led to the first goal.
Alexis Saelemakers – 5/10
Was drawn into fouling on multiple occasions, with Ivan Perisic and Son linking well down the left-hand side.
Rade Krunic – 6/10
Did not have a huge impact on the game, but teamed up well with Sandro Tonali to stop Tottenham from breaking through the lines.
Sandro Tonali – 7/10
Broke up play well, disrupting Tottenham's attacking play. Would still be running now if he had the opportunity to.
Rafael Leao – 8/10
Caused problems all night for Tottenham. His trickery and flair were too much to deal with, completing four dribbles and drawing two fouls in the opening 45 minutes. Delicious cross to pick out Thiaw who should have scored.
Brahim Diaz – 7/10
The former Manchester City player was unlucky to be denied on his first attempt, but was well-placed to head home the opener. Went missing after his goal.
Oliver Giroud – 6/10
Never had a clear-cut opportunity for himself, but set up De Ketalaere with a cushioned header which the Belgian should have tucked away.
Charles De Ketelaere – 5/10
Massive chance with his first touch, but he got his header all wrong as it came off the right side of his head and bounced wide.
Junior Messias – 6/10
Nothing to note.
Tommaso Pobega – 6/10
Nothing to note.
Ante Rebic – 6/10
Nothing to note.
Tottenham
Fraser Forster – 6/10
Made an incredible save in the build-up to AC Milan’s opener, but the rebound fell back to Diaz who headed it into an empty net.
Emerson Royal – 6/10
Did well to beat Hernandez at the back post to head back to Kane whose acrobatic effort was blocked.
Cristian Romero – 5/10
Was beaten in a duel with Hernandez in the build-up to the first goal. Deserved yellow for a sloppy tackle on Tonali as the Italian looked to break.
Eric Dier – 6/10
Dragged down Giroud and was given a harsh yellow card, meaning he will now miss the return leg. Missed a big chance with an awful header into the ground when he found himself unmarked.
Clement Lenglet – 5/10
Managed to find himself in a good attacking position after getting through two tackles, but his pullback was intercepted by Kjaer. Probably not who you wanted in that position.
Ivan Perisic – 6/10
Linked up well with Son, without creating much.
Oliver Skipp – 5/10
Dominated in midfield by Tonali. Tottenham miss the progressive play of the injured Bentancur, with Skipp struggling to pull strings from midfield. Did well to push forward and pull one back to Richarlison whose effort was blocked.
Pape Sarr – 6/10
Made an important tackle as Milan broke and Diaz looked to swivel and shoot. Was impressive in midfield, but still looked a yard slower than the AC Milan midfield.
Dejan Kulusevski – 4/10
Spent the game in Hernandez’s pocket, with the Swedish international enduring a frustrating evening in Milan.
Heung-min Son – 5/10
Looked sharp and caused Saelemakers problems, creating two Spurs chances.
Harry Kane – 6/10
Was involved in a good aerial battle with Kjaer, which the England international got the better of. Was fouled four times in the first half and won two of his aerial battles.
Richarlison – 6/10
Nothing to note.
Arnaut Danjuma – 6/10
Nothing to note.
Ben Davies – 6/10
Long-range effort sailed harmlessly over.