Five... previous encounters between Spurs and Milan

Before this season’s UEFA Champions League, Round of 16 tie, we’d met the Rossoneri eight times - four in European competition, four in friendly matches.

Here are the details - starting with a famous night at White Hart Lane where legendary former skipper Steve Perryman, then 20, helped us take a big step towards UEFA Cup glory in 1972.

05.04.72 | Spurs 2-1 Milan | Perryman at the double

The first season of the UEFA Cup saw us drawn against Milan at the semi-final stage. The first leg was our fourth game in six days following a busy Easter programme and our 60th of the season. By contrast, it was game number 37 for Milan. Milan took a shock 25th-minute lead through Romeo Benetti which silenced the 42,064 crowd. Within 10 minutes we were level. Good work by Cyril Knowles, Martin Peters and Alan Gilzean resulted in the Scot setting up Steve Perryman on the edge of the penalty area. His rasping shot beat Fabio Cudicini in the visitors’ goal. Riccardo Sogliano was sent off in the 61st minute by Spanish referee Mariano Iglesias for twice delaying a free-kick. Four minutes later, Perryman notched the winning goal. A defensive header to clear a corner fell to him outside the penalty area and he drove in a 25-yard volley. What a night!

Spurs: Jennings, Kinnear, Knowles, Mullery, England, Naylor, Gilzean, Perryman, Chivers, Peters, Coates (Neighbour).

19.04.1972 | Milan 1-1 Spurs | The Italian job

Alan Mullery stunned the 68,482 San Siro crowd with a sixth-minute strike in the second leg of our UEFA Cup semi-final in 1972. Cyril Knowles' cross was beaten away as far as Martin Chivers, whose shot was blocked. From the rebound, Steve Perryman rolled the ball to the right for Mullery to hit a 25-yarder into the top corner, a stunning effort. Mike England saw his header under pressure from a swerving cross rebound from his own crossbar and he went close at the other end, forcing Cudicini to punch over the bar. Phil Beal brought down Alberto Bigon with 20 minutes remaining and Rivera equalised from the resultant penalty. We held out under intense pressure for the last 20 minutes to claim a 3-2 aggregate win and a place in the all-English final against Wolves, a final we also won 3-2 on aggregate to lift the first-ever UEFA Cup.

Spurs: Jennings, Kinnear, Knowles, Mullery, England, Beal, Pratt (Naylor), Perryman, Chivers, Peters, Coates.

15.02.2011 | Milan 0-1 Spurs | Crouch the hero in the San Siro

Seven-times winners, Milan were considered Champions League royalty when we faced them during our first-ever campaign in the prestigious tournament back in 2010/11. Packed with superstars - Ibrahimovic, Robinho, Seedorf, Gattuso, Pato, Nesta and a young Thiago Silva - Milan had lifted the trophy as recently as 2007 and would go on to lift the Serie A title. Having scored goals galore in the group stage, we produced a disciplined and mature performance at the San Siro, and having held the home side, snatched the win and a vital away goal thanks to a Peter Crouch strike 10 minutes from time. We always carried a threat throughout, and the winner came from a classic counter, Aaron Lennon streaking away down the right, skipping past the final defender before squaring for Crouch to roll the ball past Marco Amelia, giving us a lead to protect back at White Hart Lane.

Spurs: Gomes, Corluka (Woodgate 58), Gallas, Dawson, Assou-Ekotto, Lennon, Palacios, Sandro, Pienaar (Kranjcar 77), Van der Vaart (Modric 62), Crouch. Substitutes (not used): Cudicini, Bassong, Defoe, Pavlyuchenko.

09.03.2011 | Spurs 0-0 Milan | A nervy night in N17

Three weeks after our 1-0 success in the San Siro, a night of real tension and nerves finally came to a jubilant conclusion as we held out for a goalless draw to book our place in the quarter-finals. Milan, who had to score at least once to remain in the competition, laid siege to our goal in the first half. Gomes saved from Ibrahimovic and Alexandre Pato, while William Gallas kept Milan at bay with a priceless goal-line clearance from Robinho's deflected shot. We improved after the break however it was still Milan who provided the threat, with Mathieu Flamini and Pato coming desperately close to forcing extra time. But we dug deep and defended superbly well as a team, Gallas and Michael Dawson magnificent at the heart of our backline. Robinho almost grabbed the goal Milan craved as the tie entered stoppage time, but he was high with his fizzing drive and the final whistle sounded moments later, the signal for the party to start!

Spurs: Gomes, Corluka, Gallas, Dawson, Assou-Ekotto, Lennon, Modric, Sandro, Pienaar (Jenas 70), Van der Vaart (Bale 62), Crouch (Pavlyuchenko 82). Substitutes (not used): Cudicini, Hutton, King, Defoe.

The friendlies...

Our first friendly was in 1986, when we beat Milan 2-1 in the third/fourth play-off at the Juan Gamper tournament in Barcelona. We trailed to Dario Bonetti's opener but struck back through Mark Falco and won it late thanks to Gary Mabbutt's header in front of 89,000 at the Nou Camp. Next up, Wembley Stadium hosted the Makita International in 1988. This time, Milan would take it 2-1 after again taking an early lead, this time 2-0 via Antonio Virdis Marco van Basten. Terry Fenwick bundled home the rebound from Paul Gascoigne's piledriver for 2-1. Our next friendly was fully 27 years later, in the summer of 2015. We faced Milan in the Audi Cup third/fourth play-off at Bayern Munich’s Allianz Arena and goals from Tom Carrolll and Nacer Chadli saw us home 2-0. Our most recent friendly was in the International Champions Cup in 2018. Staged at Minnesota Vikings’ impressive US Bank Stadium, the only goal of the game was scored by Georges-Kevin Nkoudou two minutes into the second half.

20.08.86 - Spurs 2-1 Milan (Barcelona)
14.08.88 - Spurs 1-2 Milan (Wembley)
05.08.15 - Spurs 2-0 Milan (Munich)
31.07.19 - Spurs 1-0 Milan (Minneapolis)