AC Milan took a step towards reaching their first Champions League quarter-finals in eleven years when Brahim Diaz’s goal gave Italy a 1-0 win over Tottenham Hotspur in the first leg of the last 16 at the San Siro on Tuesday.
The Spaniard headed in the seventh minute after a superb double save from Tottenham’s second-choice goalkeeper Fraser Forster and the seven-time winner kept the Londoners at bay.
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Weakened by injuries and suspensions, Spurs responded positively in the first half, dominating possession but failing to cause serious concern for the hosts.
Milan should have extended their lead after the break as substitute Charles De Ketelaere and defender Malick Thiaw both missed glorious header chances.
Tottenham sent on Brazilian striker Richarlison for the last 20 minutes and although they couldn’t avoid their first defeat by Milan they will go home still hoping to turn the tie and reach the last eight.
Milan’s record against Premier League clubs has been dismal in recent years, with just one win in 17 years before meeting Antonio Conte’s Spurs side.
But against fickle opponents who were without the suspended Pierre-Emile Hojbjerg and injured Rodrigo Bentancur in midfield and substituted goalkeeper Hugo Lloris, they deservedly ended that run with a tenacious performance.
The San Siro crowd didn’t have to wait long for some cheering as Theo Hernandez defeated Cristian Romero before firing a shot at Forster, who made a good save.
Diaz’s rebound was also brilliantly saved but he reacted quickly to bundle a header.
With 22-year-old Oliver Skipp and 20-year-old Pape Sarr in central midfield, Tottenham were able to gain a foothold and Son Heung-min’s free-kick was met with a short header by Eric Dier, but it went straight to Milan keeper Ciprian Tatarusanu.
Tatarusanu then made a good save from Son, with Harry Kane hitting the rebound against the crossbar, although a goal would have been disallowed for offside anyway.
Spurs huffed and puffed after the break with little reward and were lucky Milan didn’t create a bigger cushion for the second leg in March.
Within minutes, De Ketelaere headed wide after Olivier Giroud headed the ball back over the goal and then Tottenham took another jab as Thiaw also went wide with an equally inviting chance.
Dier, suspended for the second leg, should have done better with a chance at the other end but the visitors couldn’t complain about the end result.