Brahim Diaz's first goal since October gave AC Milan a 1-0 victory over Tottenham in the first leg of their Champions League round of 16 tie.

Diaz had gone 12 games without a goal for the Serie A champions but stunned Spurs with an early header on Tuesday.

Tottenham saw plenty of the ball but were unable to come up with an equaliser on former Inter boss Antonio Conte's return to San Siro.

Milan had been without a win in seven matches before beating Torino last Friday, but Diaz gave them back-to-back victories and a slender advantage to take into the second leg at Tottenham Hotspur Stadium on March 8.

San Siro erupted when Diaz opened the scoring in the seventh minute, diving to nod in on the goal-line after Fraser Forster produced a brilliant double save to deny the Spaniard and Theo Hernandez.

Spurs responded well to that early blow, though did not create a clear-cut opportunity until Harry Kane rattled the crossbar just before the break, but an offside flag against Son Heung-Min meant the striker's effort would not have counted if it had found the back of the net.

There was concern for Milan when goalkeeper Ciprian Tatarusanu appeared to go over on his ankle before Eric Dier was shown a yellow card that will rule him out of the second leg.

Conte introduced Richarlison with 20 minutes to go before Charles De Ketelaere and Malick Thiaw wasted glorious chances to extend Milan's lead with headers from close range.

Tottenham applied some late pressure, but lacked the quality to salvage a draw and have work to do next month.

What does it mean? Advantage Milan as Spurs lack invention

This was a first victory for Milan in a competitive game against Spurs in five attempts. having lost two and drawn as many in their previous four meetings. They had not defeated an English side in the Champions League since beating Arsenal back in 2012.

It was also a sweet victory over Conte, who had come out on top in eight of his past nine matches against the Rossoneri.

Tottenham were hammered 4-1 at Leicester City in the Premier League last Saturday and will need more creativity in order to mount a fightback in London and reach the quarter-finals.

Diaz ends goal drought

It has been a long wait for a goal for Diaz, but he picked a big game to end his drought.

The 23-year-old is the youngest player to score for Milan in a Champions League knockout game since Kaka struck against Deportivo La Coruna at the quarter-final stage when he was 23 years and 336 days old in March 2024.

His goal, timed at six minutes and 24 seconds, was the fastest for Milan in a Champions League knockout game since Ronaldinho netted after two minutes and 11 seconds against Manchester United in February 2010.

Son's struggles continue

Tottenham have not had Son firing on all cylinders this season and he failed to make his presence felt as Kane was starved of service.

Son did not have a single touch inside the Milan box and Conte must have been tempted to haul him off earlier than when he was replaced by Arnaut Danjuma after 81 minutes.

Key Opta Facts

- Tottenham are the first English side to lose four Champions League knockout stage games in a row since Arsenal between 2016 and 2017.
- Milan enjoyed their first Champions League knockout victory since beating Barcelona 2-0 in February 2013 in the last 16, losing each of the three since then.
- Rafael Leao completed nine dribbles in this game, the most by a player in a single match in the Champions League this season and the most by a Milan player since Opta started collecting this data (2003-04).
- Kane made his 66th appearance for Tottenham in major European competitions, the joint-most of any Spurs player, level with Hugo Lloris.
- Son appeared in his 54th game in the Champions League, the joint-most of any Asian player in the history of the competition, level with Park Ji-Sung.

What's next?

Milan face Monza in Serie A on Saturday, while Spurs have a home London derby against West Ham on Sunday.