AC Milan 1 – 0 Tottenham

Brahim Diaz’s early goal condemned Tottenham to a 1-0 loss against AC Milan in the first leg of their Champions League last-16 tie at San Siro.

Former Manchester City winger Diaz bundled home from close range after seven minutes and Spurs were fortunate not to fall further behind in the closing stages when Milan spurned two glorious headed chances through Charles De Ketelaere and Malick Thiaw.

Instead, Antonio Conte will be relieved to return to north London with a deficit of only one goal having been forced to field a central midfield pairing of Oliver Skipp and Pape Sarr due to Rodrigo Bentancur’s injury and the suspension of Pierre-Emile Hojbjerg.

Skipp and Sarr performed well in difficult circumstances on their full Champions League debuts but, in a largely cagey encounter, Spurs, beaten 4-1 by Leicester in the Premier League on Saturday, were unable to create any clear scoring chances.

Their personnel issues will continue in the second leg at the Tottenham Hotspur Stadium, with a yellow card to Eric Dier meaning he will miss out through suspension, but the one-goal margin of defeat means the tie is still open for Conte and his players.

How Milan claimed their win

Conte claimed some of his players struggle to cope with pressure after the 4-1 loss to Leicester and, at a hostile San Siro, Milan’s early opener seemed to provide further evidence.

The goal came after Theo Hernandez beat Cristian Romero to a long pass on the left and forced a parry from Forster, who then acrobatically saved Diaz’s follow-up, only for the winger to force the loose ball into the net with a diving header.

Spurs were having to work hard to contain the dangerous Rafael Leao but they slowly settled into the game after the early goal, causing problems for the hosts with a series of set-piece deliveries, albeit without creating any clear chances in the first half.

The second period began with a let-off for the reckless Romero, who was only booked, with VAR upholding the decision not to send him off, after he went flying into Sandro Tonali as Milan sprang forward on the counter-attack.

The game continued to follow a similar pattern after that, with Leao the only player providing a spark and Spurs struggling to turn their possession into scoring opportunities.

Conte threw on Richarlison for Dejan Kulusevski in an attempt to increase his side’s attacking threat but all they could muster were occasional half-chances, with Sarr sending a long-range effort straight at Milan goalkeeper Ciprian Tatarusanu.

The hosts then had two golden opportunities to ram home their advantage, with De Ketekaerem, on as a substitute only moments earlier, heading tamely wide after Oliver Giroud had nodded a cross back into the danger area, and defender Thiaw then doing the same when picked out by Leao in an even better position.

Dier failed to connect properly with a header of his own, from a corner, as Spurs attempted to punish those Milan misses at the other end of the pitch, but they never really looked like scoring.

Conte: Our fans can help us go through

Spurs head coach Antonio Conte told BT Sport: “I think it was better today and high intensity and I think we played against a good team. Don’t forget Milan last season won the league in Italy.

“I think that to concede the first goal, we can do much better. Instead we concede a goal after maybe only five minutes. Then we try to lead the game and create a situation to score but I think Milan defend very well.

“We created the chances to score but in the end we are talking about a defeat, a loss.

“For qualification you have to play two games. It is the first game away and the atmosphere was fantastic. I know the San Siro and I know the difficulty to play with this atmosphere.

“In the second game we have to play at our stadium and our fans will create the atmosphere to help us overcome the Milan obstacle.”

Analysis: Sarr, Skipp positives for Spurs

Antonio Conte will rue the defensive sloppiness that allowed Brahim Diaz to score AC Milan’s winner but there were positives for him to take too. First, that the tie is still open ahead of the second leg. And second, the performances of Pape Sarr and Oliver Skipp.

Sarr had never previously featured in the competition. In fact, this was only the 20-year-old’s sixth appearance for Spurs in any competition. But together with Skipp, a full Champions League debutant himself at 22, he did not look out of place.

The pair were thrust into action due to circumstance, of course, with Pierre-Emile Hojbjerg suspended and Rodrigo Bentancur joining the injured Yves Bissouma on the sidelines when he ruptured his ACL in Saturday’s 4-1 loss to Leicester in the Premier League.

But up against a vastly more experienced midfield duo of Sandro Tonali and Rade Krunic, they competed well, using the ball tidily and, in Sarr’s case in particular, defending tigerishly. The Senegal international made five tackles and regained possession 12 times – four more than anyone else on the pitch.

“It’s nice to have the manager’s trust,” Skipp told BT Sport afterwards, before Conte added, in his own interview, the academy product and his younger team-mate had “repaid” that trust. “I’m really satisfied for both players,” added the Spurs boss.

In Hojbjerg, Conte should have at least one of his missing midfielders back for next month’s second leg, but Sarr and Skipp have shown they can deliver when called upon. “To have this kind of performances from Skippy and Sarr makes me more relaxed because I know I can trust them 100 per cent,” added Conte.

Leao’s dazzling dribbles – Opta stats

• 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).
• Milan have beaten Tottenham in European competition for the first time at the fifth attempt (D2 L2), and it’s their first victory in their last 10 against English opposition (D1 L8), since a 4-0 win over Arsenal in 2012 in the Champions League.
• Tottenham are the first English side to lose four Champions League knockout stage games in a row since Arsenal between 2016 and 2017, with Antonio Conte’s side failing to score in each of those fixtures.
• 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.
• Harry Kane made is 66th appearance for Tottenham in major European competitions, the joint-most of any Spurs player, level with Hugo Lloris.

What’s next for Spurs?

Sunday 19th February 4:00pm


Kick off 4:30pm

Tottenham return to Premier League action with a home game against West Ham, live on Sky Sports Premier League on Sunday from 3.30pm; kick-off 4.30pm.

Spurs will play the second leg of their Champions League last-16 tie with AC Milan on Wednesday March 8 at Tottenham Hotspur Stadium; kick-off 8pm.