Milan hold the advantage heading into the second leg of their UEFA Champions League round of 16 tie against Tottenham. But who will be advancing into the quarterfinals? Here’s our preview and prediction ahead of Wednesday’s game.  

Tottenham vs Milan: The Quick Hits

  • Tottenham the favourites to win on Wednesday night, but Opta prediction states Milan to advance into the quarter-finals.
  • Does the supercomputer know something we don’t? Looks like we might be headed for extra-time and perhaps penalties at the Tottenham Hotspur Stadium
  • Harry Kane set for a record-breaking appearance, but can he end this Champions League goal drought?

Match Preview

Two sides that suffered defeats on Saturday in their respective leagues go head-to-head in London on Wednesday, with a place in the UEFA Champions League quarter-finals at stake. 

Despite registering 21 shots, Tottenham Hotspur couldn’t find their way past Wolves this past weekend as they slipped to a 1-0 defeat. It wasn’t quite as dramatic for Milan, although Theo Hernandez’s strike would only be a late, late consolation as they suffered a 2-1 defeat on the road against Fiorentina. 

It’s the Serie A side holding the advantage heading into the second leg at Tottenham Hotspur Stadium following a 1-0 triumph at the San Siro three weeks ago. It was their third win in a row in the competition, as many as they had in their previous 17 in the UCL. (D5 L9). 

But something is going to have to give on Wednesday. Milan have won just one of their last 14 away games in Champions League knockout stages (D6 L7), whilst Tottenham have lost each of their last four UCL knockout games dating back to their underwhelming final against Liverpool in the 2018-19 season, failing to score each time. 

Previous Meeting

Milan 1-0 Tottenham Hotspur – 14 February 2023 (UEFA Champions League, Round of 16 – First Leg)

Milan 1-0 Tottenham Hotspur xG Shot Map

The latest game in that Tottenham run – a poor spell of UCL results preceded by the come-from-behind victory against Ajax that sent them to the 2018-19 final – saw Milan register their first ever victory over Spurs in a European competition at the fifth attempt. 

Brahim Diaz netted the only goal of the game after seven minutes, but Milan may come to rue a pair of headers from Charles de Ketelaere and Malick Thiaw that went just past the post from close range and could have given them a two- or three-goal cushion heading into the second leg. 

Tottenham did control possession for much of the game, but a front three of Harry Kane, Son Heung-min and Dejan Kulusevski found it hard to break down a strong Milan backline. And, with the need to get a result potentially opening things at the back, they won’t be helped by Eric Dier being suspended for the return leg.  

Milan 1-0 Tottenham xG Race Chart

Recent Form

One of the challenges for Spurs in the UEFA Champions League this season as been the consistency of goal scoring. They’ve failed to score in both halves in any of their seven games so far this season, even failing to score at all on three separate occasions. 

They’ve also conceded the first goal in five of their seven Champions League games this season. That will be somewhat of a worry as the 13 goals Milan have scored so far this campaign is their most in a single campaign since 2011-12. 

The Italian side came through in second place in Group E, at what proved to be a relative canter, despite losing two games – both to eventual group winners Chelsea. It’s part of a rather unwanted record that has seen Milan win just 26% of their Champions League games against English sides (W6 D6 L11), their lowest win rate against sides from any nation (minimum three meetings). 

Despite going on to win Group D, it proved a slightly harder task for Tottenham, registering just one more point than Milan (11) in doing so. A campaign that saw them stumble to defeat against Sporting CP in the second round of fixtures eventually ended with a dramatic victory over Marseille when at one point earlier in the day, it looked like they would be crashing out. 

It does feel like we can be certain of goals though at Tottenham Hotspur Stadium, the last seven UEFA Champions League games there have seen a total of 30 goals scored at an average of 4.3 per game. But Spurs’ only goalless draw in 25 home games in the competition did come in their only such meeting with Milan back in March 2011. 

Players to Watch

Tottenham Hotspur: Harry Kane

It will be a record-breaking moment for Harry Kane upon kick-off on Wednesday night. With Hugo Lloris ruled out, the England captain will make his 67th appearance for Tottenham in a major European competition and move clear of the Frenchman as the club’s all-time leader. 

How dearly would he love to celebrate it with a goal? There are many reasons, among them the fact he’s netted just once in his seven UEFA Champions League appearances this season after scoring 20 in his first 24 appearances in the competition. 

Harry Kane UEFA Champions League 2022-23 shotmap

Following a disappointing week that saw Spurs exit the FA Cup against Championship side Sheffield United and their top-four hopes in the Premier League take a serious knock, Kane blasted the team for not being more clinical in front of goal. The captain will need to lead from the front on this occasion and add to the six goals he’s scored in his last six Champions League games on home soil to push his side into the quarter-finals. 

Milan: Olivier Giroud

He’s previous haunted Tottenham as both an Arsenal and Chelsea striker. And now Oliver Giroud has the chance to do it on the European stage with the Frenchman in particularly fine form for the Serie A giants this season. 

Giroud has been involved in six goals (four goals, two assists) in his last six UEFA Champions League appearances. Impressive considering this is twice as many as any other Milan player this season. Much like Kane there is some debate about whether he will stay at his current club come the end of the season, with the 36-year-old open to a return to the Premier League. 

It might mean this could be his final chance to become the second Frenchman to score 5+ goals in a single Champions League campaign for three different clubs, having previously scored six for Chelsea (2020-21) and five with Arsenal (2015-16). The other Frenchman was another north London foe of Spurs, Thierry Henry (Monaco, Arsenal and Barcelona). 

Tottenham vs Milan Prediction

Tottenham vs Milan Prediction

There’s some good news for Spurs players and fans according to the Opta supercomputer, with our prediction making them favourites to win against Milan in the second leg on Wednesday at Tottenham Hotspur Stadium. 

Whether the 49.3% chance they are being given of victory will be enough to avoid either extra-time or penalties is unknown, but Tottenham have progressed from two of their last three European ties when losing the first leg, most famously against Ajax in the 2018-19 UEFA Champions League semi-final but also against Pacos de Ferreira in qualifying for the 2021-22 Europa League.  

The trouble is the remaining 50.7% chance of either a draw or Milan victory is making the Italian side favourites to advance, although Milan have only ever won one of their 21 away games against English sides in all European competitions. They have also only been eliminated in three of their 21 previous European Cup/UEFA Champions League knockout ties when winning the first leg – the last time that occurred being back in 2012-13 against Barcelona. 

Even if Milan advance into the quarter-finals, their chances of winning an eighth European Cup are pretty slim (2.41%), some way behind that of outright favourites Bayern Munich (26.85%), Manchester City (18.12%), Napoli (16.7%) and Real Madrid (11.91%). Such is the mountain that Tottenham must climb, their own chances of overall success are rated at just 1.04%. 

Enjoy this? Subscribe to our newsletter to receive exclusive stories each Friday. It’s free. And follow us on Twitter too.