Tottenham loses to Milan in a close first-leg match

After Brahim Diaz gave AC Milan a slim victory in the first leg of their round-of-16 match at the San Siro, Tottenham will need to mount a Champions League comeback.

Theo Hernandez’s original follow-up attempt was brilliantly stopped by Spurs goalkeeper Fraser Forster, who also saved Diaz’s initial attempt.

Long stretches of the match against the seven-time European winners saw Antonio Conte’s team appear relatively at ease as Pape Sarr and Oliver Skipp, a young midfield duo, effectively filled in for Pierre-Emile Hojbjerg’s suspension and Rodrigo Bentancur’s injury.

Harry Kane, Son Heung-min, and Dejan Kulusevski, up to his withdrawal, were their front three, but they were hardly able to generate much forward momentum due to a well-organized home defense.

Conte’s team looked most capable of posing a threat from set-pieces, aside from speculative long-range attempts from Emerson Royal and Sarr, but neither Kane nor Eric Dier were able to guide headers on goal from two superb Son deliveries.

In the end, Spurs were appreciative of the hosts’ carelessness as German defender Malick Thiaw and Belgian midfielder Charles de Ketelaere both missed golden opportunities to give the Italian team a strong lead in the match.

If either had nodded in from close range, Spurs would have had a considerably harder time recovering for the second leg on March 8 in London.

As it stands, they will have to try to win the game without Dier because he will be suspended for receiving a second-half booking.

Tuesday’s complete Champions League commentary
Podcast for football every day: Milan on Valentine’s Day for UCL away days
Milan keeps winning against Spurs
Stefano Pioli’s team made a terrible start to 2023 with just two points from a potential 15 – falling to fifth in Serie A – before last Friday’s victory over Torino.

But even though they lack the star power or swagger of the great Milan sides, they showed sufficient of skill to eke out a slim lead.

The only thing they will look back on is that they didn’t put the match beyond a Spurs team that competed admirably but couldn’t even get a hand on them in the final third.

As things stand, advancing to the quarterfinals is still very much in doubt, though Conte will still need to come up with a solution to replace Bentancur, an important player who joined the team from Juventus just over a year ago and is a Uruguayan national.

The Argentine Cristian Romero will undoubtedly be questioned for his involvement in Milan’s victory, but the Italian will also want more tenacity from his team in defense.

In the lead-up to the goal for the home team, Hernandez outjumped the World Cup-winning center-back and left him floundering. He was later cautioned for an untimely challenge on the vivacious Rafael Leao.

Spurs’ hopes of preventing Milan from reaching the quarterfinals for the first time since 201 will depend heavily on their ability to contain the Portugal international’s frightening runs in the second leg.