An early strike from Brahim Diaz saw Milan take a 1-0 lead over Tottenham in the first-leg of their Champions League last 16 showdown.
The Rossoneri struck early in the first-half to leave the Premier League side with work to do at the Tottenham Hotspur Stadium on 8 March.
But Milan may be left to rue missed opportunities on the night to put the tie to bed.
Already without captain Hugo Lloris and Rodrigo Bentancur in midfield, Antonio Conte’s side suffered the worst possible start when they fell behind after just seven minutes.
Cristian Romero came up second best in aerial duel with Theo Hernandez, whose cross shot cannoned off the chest of Fraser Forster.
The goalkeeper produced a stunning save to bat away an effort from Brahim Diaz but the former Manchester City and Real Madrid playmaker reacted quickest to get onto the rebound, heading into the back of the net.
Spurs laboured as they chased an equaliser but failed to truly trouble Ciprian Tatarusanu in the Milan goal.
With Simon Kjaer turning in an excellent performance at the back in marshalling Harry Kane, Milan had their opportunities to double their lead.
Moments after coming off the bench in 78 minutes, Charles De Ketelaere missed a golden opportunity to score his first goal for the club, latching onto Olivier Giroud’s knockdown but getting his header all wrong.
Another big chance came and went moments later with another cross from Rafael Leao from the left causing trouble with defender Junior Messias this time heading wide.
Eric Dier, booked in the second-half which will see him suspended for the second leg, was unable to direct a header of his own on target as Spurs chased an equaliser.
But Milan held onto their valuable lead.
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