Tottenham survive late Milan chances as Brahim Diaz settles last-16 first leg

AC Milan 1-0 Tottenham: Spurs are still in this tie but were thankful that Charles De Ketelaere and Malick Thiaw missed free headers late on at the San Siro

Diaz celebrates his opening goal in the seventh minute (Getty Images)

Tottenham will have to do things the hard way if they want to progress in the Champions League after they lost 1-0 at AC Milan in the first leg of their last-16 tie.

It was an insipid display at San Siro by Antonio Conte’s side and they were unable to recover from Brahim Diaz’s early opener.

They could have been returning to London with a heavier deficit, with Ivan Perisic having to clear off the line and then Malick Thiaw sending a free header wide as the hosts finished strongly.

Conte’s men, who have been chronically inconsistent this season against a backdrop of injuries to key players, will have to be much better in the return leg in three weeks if they are to have any hope of overturning Milan’s lead.

They have history of Champions League comebacks, with their run to the 2019 final littered with late twists, though this current crop seem a million miles away from that side under Mauricio Pochettino.

Milan, who were winless in seven games prior to Friday’s victory over Torino, are likewise a far cry from the outfit that eased to the Serie A title last season but Spurs barely threatened their goal despite plenty of possession and territorial advantage.

Despite that poor run of form, the Milan fans wanted to show just how much they loved their side on Valentine’s Day and before kick-off held up tifo signs saying ‘I’m not cheating on you’.

And the hosts were quick to give their adoring faithful a present as they went ahead with less than seven minutes on the clock.

Theo Hernandez got the better of Cristian Romero in an aerial challenge on the right and saw his shot saved by Fraser Forster, who then produced a brilliant stop to deny Diaz from the follow-up. However, the smallest player on the pitch was able to nod the second rebound home from point-blank range.

Diaz scores the opening goal (Getty Images)

It was the travelling Tottenham fans who were left feeling betrayed by an all-too familiar pedestrian and passive start from their side.

They did began to get a foothold in the game and had numerous opportunities to test the Milan defence from set-pieces, but a host of corners and free-kicks were wasted by poor deliveries or defended well by the hosts.

The majority of the first half was being played in Milan’s half but Emerson Royal’s long-distance shot that was safely swallowed up by Ciprian Tatarusanu was Tottenham’s best effort.

The second half saw a resumption of what happened before the break – Spurs in control of the game but lacking the quality to threaten a leveller, with more set-piece deliveries wasted.

There were some problems at the other end as Romero was booked for a reckless tackle on Sandro Tonali while Eric Dier picked up a yellow card which will see him suspended for the second leg.

Harry Kane barely saw a goalscoring chance (Getty Images)

Spurs could not make any headway and instead it was the hosts who finished the game looking for a killer second.

Perisic had to make a last-ditch clearance from Charles De Ketelaere’s goalbound header and then Thiaw was in acres of space from Rafael Leao’s cross but put his header wide from six yards.

Dier had a free header from yet another corner but made a mess of it to leave Spurs needing to turn the tie around on home soil.