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Spurs logo
Champions League | Round of 16 | 2nd Leg
Mar 8, 2023 at 8.10pm UK
Tottenham Hotspur Stadium
Milan logo

Spurs
0 - 0
AC Milan


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Tottenham Hotspur vs. AC Milan head-to-head record

Ahead of Wednesday's Champions League last-16 second leg between Tottenham Hotspur and AC Milan, Sports Mole looks at the head-to-head record between the two clubs.

With ninety minutes separating them from European agony or elation, Tottenham Hotspur host AC Milan in the second leg of their Champions League last-16 tie on Wednesday evening.

The Lilywhites succumbed to a 1-0 defeat in the first leg at San Siro courtesy of Brahim Diaz's winner, which marked Antonio Conte's most recent game in the dugout before he ceded duties to Cristian Stellini while recovering from gallbladder surgery.

The Premier League and Serie A title-winner is now back in control of the reins ahead of the visit of the Rossoneri, who could all but end Tottenham's hopes of silverware for the 15th season running in North London this week.

Here, Sports Mole takes a closer look at Tottenham and AC Milan's head-to-head record ahead of Wednesday's pivotal showdown.


AC Milan's Brahim Diaz celebrates scoring their first goal with Theo Hernandez on February 14, 2023© Reuters

Wednesday's contest will mark the sixth meeting between Tottenham and AC Milan in any competition, and the Italian champions were forced to wait patiently for their first-ever win against the Lilywhites.

From their five previous showdowns, Tottenham have two wins to their name, while another two contests have ended with the spoils shared, and Milan were without success versus their North London counterparts until Diaz's seventh-minute strike at San Siro three weeks ago.

First locking horns in the semi-finals of the 1971-72 FA Cup, Tottenham came from behind to record a 2-1 first-leg win at White Hart Lane thanks to Steve Perryman's brace, which cancelled out an opener from Romeo Benetti.

A subsequent 1-1 draw at San Siro - where Alan Mullery struck with just seven minutes on the clock before Gianni Rivera levelled - was enough to send Tottenham into the final, where they would defeat Wolverhampton Wanderers 3-2 over two legs to lift the European trophy aloft.

Tottenham Hotspur's Pape Matar Sarr in action with AC Milan's Rade Krunic on February 14, 2023© Reuters

Nearly 40 years on from their maiden meetings, Milan would welcome Spurs back to Lombardy in the last 16 of the 2010-11 Champions League, but not even the indomitable San Siro atmosphere was enough to quell the Harry Redknapp-led Lilywhites.

Peter Crouch's 80th-minute strike secured a memorable first-leg win for Spurs, although that contest will forever be best remembered for the volatile Gennaro Gattuso's set-to with ex-Rossoneri man Joe Jordan, in what ultimately proved to be the former's final-ever appearance in Europe.

Working without the suspended Gattuso for the second leg at White Hart Lane, Milan - then under the tutelage of Massimiliano Allegri - laboured to a goalless draw to crash out of Europe for another year, although Real Madrid would proceed to make light work of Tottenham in the quarter-finals.

Now with a two-game unbeaten home run against Milan to protect, Tottenham set out to prolong the Italian champions' misery on British soil, as the Rossoneri have won just one of their 21 games away from home against English teams and have gone down 9-1 on aggregate in their last three trips to London.


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