AC Milan got a rare victory over a Premier League side as they beat Tottenham Hotspur 1-0 in the first leg of their Champions League round of 16 tie today.
Brahim Diaz scored the only goal in the first half as the Rossoneri earned a narrow win over the north London club at the San Siro.
They had previously met four times in the competition, and Tottenham were unbeaten (W2, D2).
AC Milan came into the game following a wretched January that saw them drop from second to fifth in Serie A.
They also lost the Italian Super Cup to rivals Inter Milan in that poor run. However, they secured a 1-0 victory over Torino to end their losing run last weekend.
Tottenham have also been wildly inconsistent lately. They beat Manchester City before losing to Leicester City on Saturday.
They have looked defensively fragile, but they must have fancied themselves against Milan.
Stefano Pioli played a back three, matching his opponents with Theo Hernandez and Alexis Saelemaekers as wing-backs.
The Serie A champions looked sharper and more cohesive early on, with Rafael Leao a constant danger. When Spurs doubled up on him, it allowed Hernandez to get forward.
The Milan captain beat Cristian Romero in an aerial duel before shooting at Fraser Forster, who stayed big to save. But the rebound fell for Diaz, who took two bites of the cherry to score the opening goal after only seven minutes.
Milan defended deep and repelled everything Tottenham threw at them. Simon Kjaer marked Harry Kane judiciously, although he should have been booked for multiple fouls on the England forward.
Malick Thiaw was imperious for Milan again, continuing his recent defensive form.
Before the half-time whistle, Kane hit the underside of the bar following a Heung-min Son shot, but the South Korean was offside.
Charles Ketelaere and Junior Messias came on for Stefano Pioli’s side in the second half. They both missed huge chances to increase the lead.
Despite the misses, Milan held on for a deserved win and will travel to London confidently. If they can replicate this performance on March 8, they will likely qualify for the quarter-finals.
There are more worries for Tottenham boss Antonio Conte as his side looked second best today.
They were beaten comprehensively and barely created anything noteworthy while being susceptible at the back.
Spurs now face a fight to make it through to the next round with this slight first-leg deficit.
They will hope they can gather momentum against Chelsea, West Ham United and Wolverhampton Wanderers in the league before welcoming Milan to the Tottenham Hotspur Stadium next month.