AC Milan will travel to North London next month with a slender advantage in their UEFA Champions League (UCL) round of 16 tie with Tottenham Hotspur after Brahim Díaz’s early goal guided the Rossoneri to their first-ever competitive victory over Spurs.
Friday’s unconvincing yet crucial 1-0 win over Torino ended a miserable seven-game winless run for Milan who were making their first appearance in the UCL knockout rounds in nine years.
They marked their long-awaited return to the last 16 with a goal inside seven minutes despite Fraser Forster, who was playing his first UCL game since 2013, doing his utmost to keep the hosts at bay.
First, the Tottenham goalkeeper denied Théo Hernandez, and he so nearly pulled off a miraculous save to thwart Díaz, but the Real Madrid loanee reacted quickest to bundle the ball over the line on the rebound.
Spurs were off the boil in Saturday’s demoralising 4-1 defeat to Leicester CityAMP, and they continued to offer very little in the first half at the San Siro until Son Heung-min forced Ciprian Tătărușanu into a fine stop.
Harry Kane promptly followed up to thump the ball against the crossbar before the assistant eventually raised the offside flag.
After conceding 18 goals in seven games across all competitions in January, Milan boss Stefano Pioli has switched to a back three in recent games, and their newfound resilience was stifling Tottenham’s attacking efforts.
With Milan’s rearguard remaining watertight, Pape Matar Sarr attempted to mark his first UCL appearance with an ambitious long-range effort, which was comfortably gathered by Tătărușanu.
Within a minute of entering the field of play, Rossoneri substitute Charles De Ketelaere wasted a golden opportunity to grab a second, heading wide from close-range.
Just moments later, Milan players and supporters had their heads in hands once again when Malick Thiaw failed to keep his header on target after rising high to meet Rafael Leão’s teasing delivery.
As it proved, an attritional first leg failed to produce another goal, ensuring the tie remains on a knife-edge.
Pioli can celebrate the fact his first UCL knockout game as manager ended in a victory, while consecutive defeats will be a slight concern for Spurs manager Antonio Conte on his return to the San Siro.