0-1 v AC Milan - 14 February 2023 - Away

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.

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.

Prior to last Friday's victory over Torino, Stefano Pioli's side had endured a miserable start to 2023, picking up just two points from a possible 15 - and slipping to fifth in Serie A.

However, while they do not possess the star quality or swagger of the great Milan sides, they displayed plenty of know-how to carve out a slender lead.

Their only regret will be not to have put the tie beyond a Spurs side that competed well but barely laid a glove on them in the final third.

As it is, a place in the quarter-finals very much hangs in the balance, although Conte will still have to figure out a way to compensate for the loss of Uruguay international Bentancur, who has become a key player since arriving from Juventus just over 12 months ago.

The Italian will also demand greater diligence in defence from his side with Argentine Cristian Romero sure to come under scrutiny for his role in Milan's win.

The World Cup-winning centre-back was outjumped and left floundering by Hernandez in the build-up to the home side's goal and was later booked for an ill-timed challenge on the lively Rafael Leao.

Stopping the Portugal international's menacing runs in the second leg will be critical to Spurs' hopes as they bid to prevent Milan from reaching the quarter-finals for the first time since 2012.