AC Milan and Tottenham Hotspur meet at the Stadio Giuseppe Meazza on Tuesday evening in the first leg of their UEFA Champions League round of 16 tie. We preview the game and reveal who our Opta predictor thinks will win.
Milan vs Tottenham: The Quick Hits
- The Opta Supercomputer predicts that Milan will win this UCL home game against Tottenham on Tuesday night.
- The pre-match predictions are close, however, with Spurs boss Antonio Conte having an excellent recent record in games against Milan.
- Harry Kane is on the hunt for his 20th competitive goal of the 2022-23 season for Spurs.
Match Preview
Milan and Tottenham will meet for just the fifth time in a competitive match when they face each other at the San Siro on Tuesday night in the UEFA Champions League.
Spurs are unbeaten in all four of their previous head-to-heads against Milan, with two wins and two draws – both over two-legged European ties. In 1971-72, Spurs beat Milan 2-1 at home in the UEFA Cup semi-finals before drawing 1-1 away to qualify for the final, where they defeated fellow English top-flight club Wolves 3-2 over two legs.
Spurs did it again in the 2010-11 Champions League. First they picked up a famous 1-0 win in Milan, before playing out a goalless draw at White Hart Lane to reach the quarter-finals of the competition for the first time.
That win over Milan at the Giuseppe Meazza is their solitary victory in three Champions League trips there, having lost in the stadium to Inter Milan twice in the competition (November 2010 and November 2018).
Milan have had a nine-year wait to play a Champions League knockout tie, with their last KO stage appearance in the competition coming back in 2013-14 where they lost emphatically to Atlético Madrid over two legs in the round of 16 (5-1).
Spurs will hope Antonio Conte is their lucky charm for this tie. Their manager’s previous form against Milan is excellent, having won eight of his last nine games as a boss versus the Serie A giants between 2013 and 2021. On the last three occasions that he’s taken a team away to play at the San Siro versus the Rossoneri, they’ve won and kept a clean sheet (all in Serie A).
Previous Meeting
Tottenham 0-0 Milan: 9 March 2011 (UEFA Champions League)
Spurs’ 0-0 draw with AC Milan at White Hart Lane in March 2011 might not have seen any goals, but it was a typical action-packed night of Champions League action. After famously winning the first leg at the San Siro 1-0 thanks to Peter Crouch’s finish following a lung-busting run from Aaron Lennon, Spurs managed to hold onto their slender lead in the home leg despite coming under plenty of pressure from the Italian giants.
At the time of this fixture, Milan were riding high as Serie A league-leaders – five points ahead of rivals Internazionale – and had lost just one of their previous 14 competitive games (that coming in the first leg versus Spurs). Tottenham kept out the likes of Zlatan Ibrahimovic, Robinho, Alexandre Pato and Clarence Seedorf that day, thanks to some smart saves from Heurelho Gomes and a dramatic goal-line clearance from William Gallas.
Across the two-legged last 16 tie, the Brazilian goalkeeper made six saves without being beaten to help Spurs manager Harry Redknapp become the first English coach to qualify for the UEFA Champions League quarter-finals.
The second leg of this tie wasn’t as heated as the first in Milan, where a touchline fracas between Joe Jordan and Gennaro Gattuso followed an awful two-footed lunge by Milan (and former Arsenal) midfielder Mathieu Flamini that saw Vedran Ćorluka leave the pitch on a stretcher.
You can see the best of the action from the two legs, here.
Recent Form
Milan entered the winter break – enforced by the 2022 FIFA World Cup in Qatar – in a solid position; in second place and just eight points off leaders Napoli. However, a disastrous run of form in 2023 has seen them head into this UCL tie with doubts about their quality.
Of the nine competitive matches that Milan have played in 2023, they have won just two and lost on five occasions. However, they will be buoyed by a win on Friday night in Serie A against Torino, thanks to an Olivier Giroud strike. That victory prevented Stefano Pioli’s team from losing five in a row within a single season for the first time since 1929-30 after four previous defeats against Internazionale (Super Cup and Serie A), Lazio and Sassuolo.
Tottenham come into this game following a woeful 4-1 away defeat in the Premier League at Leicester City on Saturday afternoon, equalling their heaviest margin of defeat against the Foxes in the competition.
That thrashing followed a run of three successive wins and clean sheets in all competitions, including a 1-0 home victory over reigning Premier League champions Manchester City in their first game of February, as well as an FA Cup victory against Preston North End and league win away at London rivals Fulham.
In the 2022-23 UCL group stage, Tottenham topped Group D ahead of Eintracht Frankfurt, Sporting CP and Marseille with a record of 11 points from a possible 18 (W3 D2 L1). Milan, meanwhile, finished behind Chelsea in Group E, but qualified as runners-up ahead of Red Bull Salzburg and Dinamo Zagreb.
Players to Watch
Milan: Rafael Leão
It’ll be interesting to see how Portuguese Rafael Leão fares in this meeting with Spurs. The winger is at his best when finding pockets of space to run into and attack, but under Antonio Conte, Spurs have become well known for forming a low block and making it hard for opponents to find any space in behind their full backs.
A lot of Milan’s attacking threat comes through Leão, with the 23-year-old being their leading creator from open play across all competitions in 2022-23 (43 chances created) and only Giroud (17) has more competitive goal involvements than him (16) this season.
His ability to accelerate past players and his quick feet make Leão a difficult opponent for any full back. The winger had had the most shot involvements from ball carries in Serie A since the start of 2021-22 (109 – 75 shots, 34 chances created), with 14 of those ending in a goal – also a league-high over this timeframe.
So far in 2022-23, his involvement in Milan’s attacking open-play sequences highlights his threat even further, with his total of 102 being a team-high and well above the closest rivals – Theo Hernandez (77), Ismeal Bennacer (70) and Sandro Tonali (69).
Tottenham Hotspur: Harry Kane
It’s hard to look past Spurs’ new all-time record competitive goalscorer Harry Kane as their key man in this UCL match on Tuesday. Kane broke the record with his 267th Spurs goal in the 1-0 win over Man City earlier this month, surpassing Jimmy Greaves. The England captain also holds the accolade as Spurs’ leading scorer in European competitions (45), with 21 of those coming in just 30 Champions League appearances.
By full-time on Tuesday, Kane could surpass Steven Gerrard’s tally of goals (21 – the same as Kane) in the competition to become the outright-fifth highest scoring English player in Champions League history – a title that he’s only 10 goals away from holding outright ahead of Wayne Rooney (30 goals).
The 29-year-old also needs one more goal to reach 20 in all competitions in 2022-23, meaning it would be the ninth successive season that the legendary Spurs player has achieved this feat. One man looking to stop him in Italy on Tuesday night is likely to be former Chelsea central defender and fellow Englishman Fikayo Tomori, while goalkeeper Mike Maignan is considered one of the best shot-stoppers in Europe.
Milan vs Tottenham Prediction
The Opta supercomputer gives the home side the slight edge in this match, with Milan’s chance of victory rated at 37.5% compared to Spurs’ 35.1%. However, with such a small difference between each side’s win forecast, it looks like one of the hardest UCL last 16 ties to call.
Of the 16 teams remaining in the 2022-23 Champions League, neither Spurs nor Milan are being given a great chance of overall glory come the final on 10 June at the Atatürk Olympic Stadium in Istanbul, Turkey.
Only Club Brugge (0.21%) and Eintracht Frankfurt (1.27%) have a lower chance of winning the competition than the reigning Serie A champions (1.56%), while Spurs only fare slightly better in our seasonal predictions at 2.78% – making them the 11th favourites.
Bayern Munich are rated as heavy favourites (25.87%), ahead of Manchester City (18.87%), Serie A leaders Napoli (10.76%), reigning UCL winners Real Madrid (7.22%) and Liverpool (6.51%).
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