Milan vs Tottenham head-to-head record

Tottenham's most recent meeting with Milan at San Siro descended into a mass brawl
Tottenham's most recent meeting with Milan at San Siro descended into a mass brawl / Claudio Villa/GettyImages

Milan and Tottenham are two storied clubs that share a history of historic continental triumphs.

In 1963, Milan became the first Italian team to ever lift the European Cup, defeating Eusebio's cursed Benfica at Wembley Stadium. Exactly seven days earlier, Tottenham became the first English team to win a continental trophy.

Jimmy Greaves - who would briefly wear the colours of Milan - scored twice in a 5-1 triumph against Atletico Madrid to snag the Cup Winners' Cup.

These history-makers may have only faced each other four times over the years, but they've been memorable encounters. Here's the story of their past matches.

Milan vs Tottenham H2H record

Tottenham boast the bragging rights in this one-sided rivalry. Across the three European knockout ties in which these teams have met, Spurs have only been beaten once by Milan, winning twice and drawing the other two.

The pair were first drawn together in the semi-finals of the first iteration of the UEFA Cup in 1972, the forerunner to the Europa League.

Bill Nicholson's Spurs are heralded as one of the greatest English sides of the 21st century, playing a fluid and free-scoring brand of football which won trophies and admirers. Nereo Rocco's Milan were similarly successful but are closely associated with catenaccio football, a dogged defence-first (and second, and third) style.

The lead which Rocco's Milan took in the first leg at White Hart Lane lasted seven minutes. It remains the only time Tottenham have ever trailed Milan. Nicholson's side recovered to win the home tie 2-1 before battling out a 1-1 draw at San Siro which teed up a final against Wolverhampton Wanderers. Tottenham defeated the Black Country outfit 3-2 on aggregate.

Fast forward 39 years and Spurs are back in football's answer to the Scala opera house. With just ten minutes to play in the 2011 Champions League round of 16, Peter Crouch swept in the only goal of the first leg, which proved to be the only goal of the entire tie.

On a spiky night, emotions boiled over at the final whistle as Gennaro Gattuso, Milan's combative captain, squared up to Harry Redknapp's assistant manager Joe Jordan.

Jordan, who earned the nickname Jaws after losing four front teeth during a playing career which included two years at Milan, didn't flinch when Gattuso thrust his forehead towards the bridge of his nose.

Speaking after the event, Jordan revealed that Gattuso had offered an apology but menacingly conceded it was "a pity I wasn't playing".

The first leg of the 2022/23 Champions League saw Milan hold off a depleted Spurs to record a 1-0 victory heading into the second game in north London in March.

Milan vs Tottenham H2H record

Milan wins: 1
Tottenham wins: 2
Draws: 2

Top scorers in Milan vs Tottenham fixtures

There have only been seven goals in the five previous meetings between Milan and Spurs. Steve Perryman is the only man that can lay claim to more than one.

Tottenham's record appearance-maker only scored 39 goals across his entire career for the Lilywhites - 5% of which came against the Rossoneri in 1972.

After Romeo Benetti put Milan ahead in the first-ever meeting between the clubs, Perryman's brace gave Spurs a 2-1 aggregate lead to take to San Siro. Alan Mullery, another long-serving but goal-shy midfielder, broke the deadlock in the second leg of the UEFA Cup semi-final in Lombardy.

Gianni Rivera had won the Ballon d'Or three years earlier and levelled from the spot on the night but couldn't overturn the first-leg deficit.

As mentioned, Crouch scored the only goal when these sides duked it out in the Champions League a decade ago. Zlatan Ibrahimovic didn't find the scoresheet that year but the 41-year-old is the only member of either side that will be part of this year's Champions League clash, outlasting the likes of Clarence Seedorf, Robinho and Jonathan Woodgate, who were all involved 12 years ago.

More recently, Diaz's strike separated the two sides in the first leg of their 2022/23 Champions League last 16 tie.