A rather turgid affair at San Siro saw Stefano Pioli’s men score early and keep Spurs at arm’s length for most of the evening, with the Italian champions taking a one-goal lead into the return leg at the start of March.
Milan took the lead with just seven minutes on the clock. Theo Hernandez beat Cristian Romero to a high ball and fired a shot at Fraser Forster, whose chest blocked the effort. Brahim Diaz came thundering in for the rebound, and while Forster saved the initial attempt, the Spaniard’s diving header afterwards nudged the ball over the line.
Tottenham’s first half-chance came when Milan decided to defend a Son Heung-min in-swinging free-kick from 35 yards deep, allowing Eric Dier to get a glancing touch on the delivery from way inside the box, but his header went straight down the throat of Ciprian Tatarusanu.
On the stroke of half-time, Tatarusanu denied Son before Harry Kane’s rebound hit the crossbar, though the offside flag was later raised against the South Korean.
With 70 minutes played and a clear route to goal looking beyond them, Antonio Conte brought on Richarlison for Dejan Kulusevski to try and give them a spark.
The hosts nearly added a second when Rafael Leao’s cross was nodded on by Olivier Giroud and into Charles De Ketelaere’s path, but the Belgian couldn’t divert his effort from close range.
Soon after, Malick Thiaw headed just wide as Milan looked to add a second in the latter stages of the first leg.
A strike from distance by Pape Sarr trickled just wide off of Pierre Kalulu but that was as close as Tottenham came to finding an equaliser.
After six minutes of stoppage time, a low-quality match was brought to an end. Milan and Tottenham will reconvene in north London on March 8.
GK: Ciprian Tatarusanu – 6/10 – Had some real clangers recently but held his own here. Received treatment on a twisted ankle after being nudged by Lenglet.
CB: Pierre Kalulu – 8/10 – Looked very calm in his duels with Son.
CB: Simon Kjaer – 6/10 – The master of the dark-art foul. Very fortunate not to have been booked.
CB: Malick Thiaw – 8/10 – Got tight to Kulusevski and completely shut him down.
RM: Alexis Saelemaekers – 6/10 – Tracked very far back to help double up on Son.
CM: Sandro Tonali – 6/10 – Twice snapped by Romero but held his composure in a feisty midfield battle.
CM: Rade Krunic – 5/10 – Wanted a little too much time to keep hold of the ball.
LM: Theo Hernandez – 7/10 – Had the joy of the left flank for the most part. Acted like a left winger.
RF: Brahim Diaz – 7/10 – Did very well to follow up on his rebound in order to score the opener. Technically excellent but like Krunic sometimes lacked awareness of Spurs’ press.
CF: Olivier Giroud – 6/10 – Showed little in terms of hold up or making himself a nuisance in the box.
LF: Rafael Leao – 7/10 – At times looked like the best player in the world with the way he danced with the ball at his feet. At others seemed as if he’d never played the sport before. All in all, a good performance.
Substitutes
Charles De Ketelaere (77′ for Diaz) – 5/10
Junior Messias (77′ for Saelemaekers) – 6/10
Tommaso Pobega (86′ for Tonali) – N/A
Ante Rebic (90′ for Leao) – N/A
Manager
Stefano Pioli – 7/10 – Milan weren’t at their best, but they were at least resolute defensively and that was enough.
GK: Fraser Forster – 6/10 – Dives in slow motion but realistically not a lot he could have done about the goal.
CB: Cristian Romero – 3/10 – Probably his worst performance in a Tottenham shirt (in which he completed 90 minutes anyway). On another day might have been sent off for a reducer on Tonali.
CB: Eric Dier – 5/10 – An improvement on his weekend performance but that’s not saying much.
CB: Clement Lenglet – 5/10 – Reacted slowly to danger but wasn’t a complete liability in possession.
RM: Emerson Royal – 6/10 – Forced Hernandez and Leao to really work for the ball.
CM: Oliver Skipp – 6/10 – Showed bite and aggression against Tonali and Krunic.
CM: Pape Sarr – 7/10 – Stood tall and was great both in and out of possession. Tottenham’s best player by some distance.
LM: Ivan Perisic – 5/10 – Looks slowed with every passing week. Comically stumbled over prior to Diaz’s goal.
RF: Dejan Kulusevski – 4/10 – Physically doesn’t look right. Lacks the strength and quick burst he possessed even one month ago. Easily muscled out of the game.
CF: Harry Kane – 6/10 – Technically excellent but wasn’t enough of a direct threat.
LF: Son Heung-min – 4/10 – Dribbled his way out of trouble in the first half, offered nothing at all in the second.
Substitutes
Richarlison (70′ for Kulusevski) – 5/10
Arnaut Danjuma (81′ for Son) – 5/10
Ben Davies (81′ for Lenglet) – 4/10
Manager
Antonio Conte – 4/10 – Once again, Tottenham lacked dynamism and ideas. Changes should have been made much earlier in the night.
