AC Milan vs Tottenham Picks and Predictions: Can Either Side Stop the Bleeding?

For the first time in nearly a decade, AC Milan will participate in the knockout stages of the Champions League when they host Tottenham at the San Siro on Tuesday. The Rossoneri haven’t been part of the Round of 16 since losing to Atletico Madrid in the 2013-14 season, and now have an opportunity to make a run in the final season at their iconic stadium.

To do so, they will need to do something they’ve failed to do in their four other meetings with Tottenham – get a victory. Spurs have never lost to their Italian counterparts, but they’re licking their wounds following a 4-1 defeat to Leicester at the weekend.

Can Spurs continue to frustrate Milan, or will the hosts get a massive win and take pressure off their manager after a poor run of form? Find out in our AC Milan vs Tottenham picks and predictions for Tuesday, February 14. 

AC Milan vs Tottenham odds

AC Milan vs Tottenham picks and predictions

AC Milan finally ended their freefall on Friday with a 1-0 win over Torino. Their first clean sheet since before the World Cup was critical, as they ended a winless run of seven matches that saw them lose five times. During that time, they slid from second in the Serie A table down to fifth, and now sit 18 points adrift and outside the Top 4. 

Manager Stefano Pioli is still under fire after watching his team slip down the Serie A table with a nosedive that began when they conceded two late goals to blow a 2-0 lead over Roma. They’ve been eliminated from the Coppa Italia during the slide as well, leaving the Champions League as their last remaining hope for silverware.  

Meanwhile, Spurs are trying to figure out what went wrong in a 4-1 defeat to Leicester. The loss ended a three-match win streak, as defender Cristian Romero’s suspension left them bare at the back. The good news for them is that manager Antonio Conte is back on the sideline after surgery, and is very familiar with their opponent — having defeated them eight times in his last nine attempts as manager of Inter Milan and Juventus.

For Conte, this match presents a team selection nightmare. Midfielder Yves Bissouma is out with an injury, and Pierre-Emile Hojbjerg is suspended for the match. Now, he must contend with the loss of Rodrigo Bentancur, whose season ended on Saturday when he suffered an ACL tear. 

Captain and starting keeper Hugo Lloris is also sidelined, and backup Fraser Forster was left looking foolish at the weekend as he missed saves he should’ve made — although his defense didn’t help him much.

Milan are dealing with injury issues of their own, especially in goal. Mike Maignan, who had one of the best goals allowed below xG ratings in all of Europe a season ago, continues to be sidelined but isn’t far from returning. Defender Allesandro Florenzi is also absent.

What these teams do have are strikers capable of delivering if given a moment of opportunity. Harry Kane and Olivier Giroud are lethal finishers, and Heung-min Son and Rafael Leao both offer strong options from their respective left flanks. 

That’s why your best play in this contest is to stay away from a result, and instead take both teams to score. Tottenham’s back line will be heavily tested without their protection, and Milan’s been leaking goals for the past six weeks. This should be a cagey affair, but one where both teams find themselves on the scoresheet before it’s all over. 

My best bet: Both teams to score - Yes (-110 at bet365)

AC Milan vs Tottenham side analysis

Milan’s 4-2-3-1 formation should see Leao retain his starting spot after he returned to the lineup over the weekend. The win over Torino was their first in eight matches in all competitions, and just their second since returning from the World Cup. Aside from the Roma draw, all their matches at the San Siro this season have been zero-sum affairs, with 10 wins and five defeats. 

The loss of both Bentancur and Hojbjerg for this match is a massive blow to Spurs. Hojbjerg was the best player on the pitch in their 1-0 win over Manchester City, and has been a key cog in protecting the back line. His absence will be heavily felt, and Conte now likely turns to a pair of midfielders with little chemistry together — much less any experience at this level.

Milan have lost twice and drawn twice in their four previous meetings with their foes from London. While Milan are slightly favored, all three options on the 3-way line are paying out at positive odds. The draw may provide the best value, paying out better than 2-to-1 at all major books. 

AC Milan vs Tottenham Over/Under analysis

Money has been coming in heavily on the Under in this contest, and it makes sense given the loss of key players for both teams. It also falls in line with the trend for when these two clubs have squared off in the past. A total of four goals have been scored in their four previous encounters, with Tottenham scoring all of them — and only one of the four matches saw multiple goals. That said, two of those matches came in preseason tournaments.

Milan’s 1-0 win over Torino was just the second match of their last nine at home to go Under three goals — and the other one also came against Torino just a few weeks ago. For the visitors, seven of Tottenham’s last nine matches away from home have seen three or more put on the board.

Milan have kept just two home clean sheets in their last nine, while in Tottenham’s last nine they’ve kept a clean sheet three times. Both teams have scored in five of Milan’s last nine at home, and in five of Tottenham’s last nine away. 

AC Milan vs Tottenham game info

AC Milan vs Tottenham key injuries

AC Milan: Mike Maignan GK (Out), Alessandro Florenzi D (Out), Zlatan Ibrahimovic F (Out).
Tottenham: Pierre-Emile Hojbjerg M (Out), Hugo Lloris GK (Out), Rodrigo Bentancur M (Out).

AC Milan vs Tottenham weather

Fog could be an issue on Tuesday night. Milan has been dealing with it for a few days, along with very poor air quality, and while there’s no rain expected the moisture in the air could make it difficult to see. Temperatures should be in the mid-40s and winds will be minimal. 

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