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 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 then have increased their advantage after the break with substitute Charles De Ketelaere and defender Malick Thiaw both 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.
