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.
2022/2023 UEFA Champions League
1-0
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.
Had either nodded in from close range, Spurs would have faced an even more challenging recovery operation in the return leg in London on Wednesday, 8 March.
As it is, they must try to turn the tie round without Dier, who will be suspended after he collected a second-half booking.
Match Events
7' GOAL! Milan 1-0 Tottenham (Brahim)
15' Kane is taken down by Kjaer
25' Emerson's shot too straight
30' Kane's nose bleeds after collision
37' Kane rolls on the ground after taken down by Kjaer
45' Kane hits the post but offside
48' Yellow Card! Romero booked
63' Yellow Card! Dier booked
78' CLOSE! De Ketelaere’s header wide out
80' Yellow Card! Tonali booked
Line-ups
Milan XI: Tatarusanu, Thiaw, Kalulu, Kjaer, Theo, Saelemaekers, Krunic, Tonali, Brahim Diaz, Giround, Leao
Subs: Mirante, Nava, Calabria, Ballo, Rebic, Origi, Messias, Pobega, Gabbia, De Ketelaere
Tottenham XI: Forster, Romero, Dier, Lenglet, Royal, Sarr, Skipp, Perisic, Kulusevski, Son, Kane
Subs: Austin, Whiteman, Sanchez, Davies, Tanganga, Porro, Devine, Danjuma, Lucas, Richarlison