Tottenham will have to produce a Champions League comeback after Brahim Diaz gave AC Milan a narrow win in the first leg of their last-16 tie at the San Siro.
Diaz nodded in early on after Spurs goalkeeper Fraser Forster had saved a Theo Hernandez shot and then superbly got a hand on the scorer’s initial follow-up attempt.
Antonio Conte’s side looked relatively comfortable for long periods of the contest against the seven-time European champions – as a youthful pairing of Pape Sarr and Oliver Skipp deputised ably for the suspended Pierre-Emile Hojbjerg and the injured Rodrigo Bentancur in midfield.
However, they were rarely able to build any attacking momentum with their front three of Harry Kane, Son Heung-min and, until his withdrawal, Dejan Kulusevski well shackled by a disciplined home defence.
Aside from ambitious long-range efforts from Emerson Royal and Sarr, Conte’s side appeared most capable of threatening from set-pieces but neither Kane nor Eric Dier were able to direct headers on goal from two excellent Son deliveries.
In the end, Spurs were grateful for the profligacy of the hosts as Belgian midfielder Charles de Ketelaere and German defender Malick Thiaw both headed excellent opportunities – to put the Italian side firmly in control of the tie – wide.
