UEFA Champions League 2022-23: Tottenham Hotspur's Woes Continue As They Lose 1-0 To AC Milan

Brahim Díaz netted in the seventh minute to give Milan a slender advantage to take to London when the teams meet again in the second leg of the round of 16 on March 8.

But the Rossoneri could be left counting the cost of two late missed opportunities that their coach thought were going to end up in the back of the net.

“The two chances for Charles (De Ketelaere) and Malick (Thiaw) were important, I was already celebrating on the bench,” Milan coach Stefano Pioli said. “2-0 would have been a better result clearly because we are sure that the return match will be as close, as difficult.

“But I can’t be anything but happy with the team’s performance today.”

It was a miserable return to San Siro for Tottenham manager Antonio Conte, who endured only his second loss against Milan in 15 matches as coach. The former Inter Milan and Juventus coach had engineered 10 victories over the Rossoneri.

“I’m not disappointed with the performance,” Conte said. “Some of the players need to find their belief again. But there was a lot of commitment and desire from them all. My job is to show the players that I have a lot of belief in them.”

It was also Tottenham’s second straight defeat since Conte returned to the dugout following gallbladder surgery. Spurs lost 4-1 at Leicester in the Premier League on Saturday.

For Milan, it is a further sign that things might be turning around after a tough run. Milan was winless in its past seven matches, including losing its previous four matches, before Friday’s 1-0 win over Torino.

That run had seen the defending Serie A champion fall 18 points behind league leader Napoli, get knocked out of the Italian Cup and lose the Italian Super Cup to bitter rival Inter.

“Progressing to the next stage would give our season a lot more sense and positivity,” Pioli said.

The match at San Siro was Milan’s first in the Champions League knockout stage since 2014. It hasn’t reached the quarterfinals since 2012.

And the Rossoneri got their return off to the perfect start. Théo Hernandez saw his shot parried by Fraser Forster and Tottenham’s goalkeeper then did brilliantly to claw away Diaz’s effort from the rebound but the Milan midfielder bundled in from point-blank range on the second attempt.

In a tight match, there were few goalscoring opportunities and neither goalkeeper was really tested.

Ciprian T?t?ru?anu, who faced criticism during Milan’s dismal run, pulled off a fantastic double save on the stroke of halftime. He did well to deny Son Heung-min then even better to clear the danger after Harry Kane’s follow-up came off the underside of the crossbar. However, it wouldn’t have counted anyway as Son had been offside.

Milan should have wrapped up the win in the final 12 minutes but first substitute Charles De Ketelaere saw his close-range header cleared by Spurs midfielder Ivan Peri?i? and shortly afterward Malick Thiaw headed narrowly wide of the left post from six yards out.

Bayern Munich won 1-0 at Paris Saint-Germain in the night’s other Champions League match.