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AC Milan v Tottenham – Preview, Predictions, and Best Bets

AC Milan host Tottenham in the last 16 of the UEFA Champions League on Tuesday night.

Ac Milan v Tottenham

AC Milan host Tottenham in the last 16 of the UEFA Champions League on Tuesday night. Stefano Pioli’s side have been in the awful form of late with five defeats in their last seven matches. Spurs have lost seven of their last 13 league fixtures and arrive in Milano with some key players missing.

AC Milan Form

Milan have been really struggling of late. A win to start 2023 saw them on a run of three wins and one draw in four Serie A matches, placing the Rossoneri five points off Napoli at that stage. A terrible run of seven matches without a win followed. They lost 3-0 to Inter Milan in the Italian Super Cup and then 4-0 at Lazio in the league.

5-2 home shambles followed as Sassuolo destroyed an injury-hit defence. They then lost 1-0 to city rivals Inter in the league to open an 18-point gap to the summit as their title defence all but ended. On Friday, they beat Torino 1-0 at home to end their winless streak as Olivier Giroud got the winner.

AC Milan Team News

Milan’s recent struggles have largely been because of key injuries. Mike Maignan is absent in goal so veteran Ciprian Tatarusanu will cover once again. Fikayo Tomori has a small chance of being back to start in the back three that Pioli has switched to. Otherwise German youngster Malick Thiaw will get a start.

Ismael Bennacer and Alessandro Florenzi are not expected to return so Rade Krunic will start in central midfield. Zlatan Ibrahimovic is not registered for this competition up front so it’ll certainly be Giroud with Rafael Leao in support.

AC Milan Motivation

Milan can no longer retain the league title and they’re out of all domestic cup competitions. This competition represents a chance to salvage their season.

They’ll hope to win at home and have something to take to North London for the second leg. Pioli has been more pragmatic in recent games with his shape change to arrest their defensive woes.

Tottenham Form

Spurs have been in pretty poor form since October, with the coach and players lacking some motivation. Their 13 most recent Premier League matches have brought seven defeats. They’ve won five of their 10 matches in all competitions since the World Cup but two of those came in the FA Cup against lower-division opponents.

After a 2-0 home loss to Aston Villa, they scored four second-half to win 4-0 at Crystal Palace. A 2-0 home loss to Arsenal in the North London derby saw Conte’s side outclassed. They then led 2-0 away at Man City but leaked four times after half-time to lose 4-2. On Saturday, they followed successive victories – 1-0 at Fulham and 1-0 at home to Man City – with a humiliating 4-1 home defeat to Leicester having led 1-0.

Tottenham Team News

Spurs are thankful to have Cristian Romero back in the defence after a domestic suspension. He will replace Japhet Tanganga on the right of the back three. Hugo Lloris has a long-term injury in goal so Fraser Forster will play his 15th Champions League match after some experience at Celtic.

The Tottenham midfield is decimated by issues for this match. Rodrigo Bentancur is out long-term with a cruciate ligament injury whilst Yves Bissouma has had ankle surgery. Pierre-Emile Højbjerg misses out due to suspension so it’ll have to be Oliver Skipp and Pape Matar Sarr will form a makeshift engine room.

Tottenham Motivation

This is a big game for Spurs, going to a famous city and stadium. You’d expect motivation to be at its absolute maximum and they may even have had an eye on this match during their weekend defeat.

A draw would be a good result ahead of the second leg. Conte’s side are expected to sit quite deep and use fast counter attacks.

Key Stats

Milan have conceded 15 goals in their last 6 matches in all competitions

Milan have failed to score in 3 of their last 5 matches (all competitions)

Tottenham have conceded 2+ goals in 6 of their last 9 away EPL matches

Spurs have lost 3 of their last 5 away matches in the Champions League

Spurs’ Kane is 6 UCL away matches without a goal


This fixture pits two struggling teams against each other, both of whom have been leaking goals for fun. Spurs’ midfield is depleted but they have an elite front three and could quite easily outscore Milan in this one to take a first leg advantage.

Best Bet: Over 2.5 goals at 1.90
Alternative Bet: Tottenham win at 2.90
Alternative Bet: Tottenham to score over 1.5 goals at 2.50
Goalscorer Tip: Kane anytime scorer at 2.25

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James is a football analyst who writes about the tactics of the PSL and English Premier League. He holds the UEFA A coaching licence and has previously worked for several clubs in analysis roles.Twitter:

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