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AC Milan vs Tottenham prediction, odds, betting tips and best bets for Champions League first leg

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Two clubs desperate to find their best form meet in Europe’s top competition as AC Milan host Tottenham in the first leg of their Champions League Round of 16 matchups.

Both teams have seen their domestic chase for a top four spot fall flat in recent weeks, and are in dire need of a boost. AC Milan have won just three of their last nine Serie A games in Italy, while Spurs have lost six of their last 12 in English Premier League play. Both teams have also been dumped from domestic cup action as well, with Milan out of the Coppa Italia after defeat to Torino in the Round of 16, while Spurs crashed out of the EFL Cup in early November.

Chaos abounds for each side at the San Siro on Tuesday. Spurs have been as erratic as any club in Europe, beating Manchester City 1-0 in early February before laying an egg at Leicester City 4-1 just days later. It’s been like that all season, as manager Antonio Conte has been unable to foster any kind of game-to-game consistency.

In contrast, Milan were flying before the World Cup break, with just two defeats through the opening 18 games of the Serie A season. However, over the last six games, things have fallen apart, first defensively then up front. A pair of 2-2 draws gave way to a three-match league losing streak, thumped 4-0 by Lazio and 5-2 by Sassuolo. They topped Torino 1-0 last time out to gain revenge for the Italian Cup elimination, but still conceded chances at the back.

The two clubs will both be looking for a result in European competition that could go a long way towards building the confidence needed to turn their season trajectory on its head.

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AC Milan vs Tottenham odds

AC Milan are the slightest of favorites on their home field, the San Siro, but the betting market appears unsure how this match will play out. Both sides feature plus odds on the moneyline and are nearly dead even as such.

There’s also confusion over how the game will play out on the scoresheet. While it’s expected that both teams have the firepower to find the back of the net, it’s unclear whether this match will be low or high scoring. The goal total over is a slight favorite for most bookmakers, but the margin is extremely thin.


AC Milan win +155 +147 6/4 2.55
Draw +240 +233 23/10 3.25
Tottenham win +170 +169 7/4 2.70
Both teams
to score Y / N
-140 / +100 -152 / -103 4/6, 11/10 1.67 / 2.10
Over / Under
2.5 goals
-115 / -120 -110 / -120 10/11, 4/5
AC Milan -0.5 +140 +150
Tottenham +0.5 -210 -196

AC Milan vs Tottenham: Three things to know

Here are the match facts, key stats and essential lineup information ahead of the match:

AC Milan vs Tottenham match facts

  • Date: Tuesday, February 14
  • Kickoff Time: 3 p.m. ET / 8 p.m. GMT / 7 a.m. AEDT (Wed, Feb. 15)
  • Location: San Siro (Milan, Italy)
  • Official: Sandro Schaerer (Switzerland)

AC Milan vs Tottenham team news

Today’s Italian hosts are still missing goalkeeper Mike Maignan whose thigh injury kept him out of the World Cup and he remains sidelined after suffering a setback last week. His absence has been felt, as he was arguably the top goalkeeper in Serie A before his September injury. Otherwise, the news is good for Milan. Fikayo Tomori and Ismael Bennacer both returned to training and could feature, as did Alessandro Florenzi who has been absent going on five months with a torn hamstring.

Tottenham have lost influential midfielder Rodrigo Bentancur who was diagnosed with a torn ACL during the weekend’s brutal defeat to Leicester City. His presence will be critical as Spurs have been much better with him in midfield than without. Yves Bissouma is also missing from the midfield ranks with an ankle injury, while goalkeeper Hugo Lloris is sidelined with a knee injury that will keep him out until at least late March.

MORE: Complete Champions League Round of 16 matchups

AC Milan vs Tottenham key stats

  • AC Milan have never beaten Tottenham in their four all-time meetings, all coming in UEFA continental competition. They matched up twice in the 1971/72 UEFA Cup, and again in the 2010/11 Champions League. On both occasions, Tottenham won the first leg by a single goal, and the two sides drew the second leg.
  • Antonio Conte has only lost once to AC Milan in his managerial career across 14 all-time matches, coming in a 2-1 Milan derby defeat in October 2020. He has collected 10 wins and three draws against the Italian club.
  • Both clubs sit fifth in their respective domestic league, with an automatic Champions League berth next season in peril. Prior to the World Cup break both teams were in Champions League positions. AC Milan sat second in the Serie A table at the break in November, while Tottenham stood in fourth in the Premier League.
  • After collecting 10 goal involvements (5 goals, 5 assists) through the first 11 Serie A matches of the season, Rafael Leao has just four goal involvements (3 goals, 1 assist) in his last 11 league games. He has not scored or assisted a goal in his last five matches across all competitions.

AC Milan vs Tottenham prediction

  • Moneyline lean: Draw (+240)
  • Against the spread lean: Tottenham +0.5 (-210)
  • Score prediction: AC Milan 2-2 Tottenham

Plainly put, this is an extremely difficult match to parse, as both clubs have shown flashes of brilliance along with plenty of mistakes since the World Cup break concluded. Both sides have shipped goals on multiple occasions, then gone out and earned a clean sheet, only to be blasted again, all within the span of a few days or weeks.

The key to this match will be the play of Milan midfielder Sandro Tonali, who has been utterly putrid over his last five games after starring through the first half of the campaign. If he can take control of the midfield, with Spurs missing key players in the central area, Milan should hold on at home. If, however, Tonali has a performance like he did against, say, Sassuolo in late January, where he coughed up the ball repeatedly, Spurs will be a force on the break.

Tonali’s play in the Friday win over Torino suggests an upward trend, but it still left a lot to be desired, and this could end up being a chaotic match with lots of last-ditch defending on both ends.

AC Milan vs Tottenham: Best bet

  • Pick: Over 2.5 goals
  • Odds: -115 (BetMGM)

Both teams are missing their starting goalkeepers. Tottenham are missing key midfield pieces, and the AC Milan midfielders are in horrid form. This match screams chaos.

Spurs only saw two of their six Champions League group stage matches go over the 2.5 goal total, but those came against chaotic teams Eintracht Frankfurt and Olympique Marseille. While AC Milan don’t normally profile nearly as chaotic, their matches went over the total in four of their group stage matches, and the additional factors in this game seem to suggest they could find themselves all over the place, too.

And for kicks, let’s add one more wrinkle: Each of the last four times Antonio Conte faced AC Milan (all coming with Inter), the match exceeded the 2.5 goal total. Expect sloppy, messy defending to result in goals galore. 

AC Milan vs Tottenham prop bet

  • Pick: Sandro Tonali to be booked
  • Odds: +240 (BetMGM)

AC Milan’s recent downturn can almost directly be linked to a dip in form for their lynchpin midfielder Sandro Tonali. He has struggled mightily since returning from the World Cup break, and while he looked to turn things around somewhat against Torino last time out, it wasn’t exactly a renaissance performance for the 22-year-old.

When on, he’s one of the best young No. 6/No. 8 hybrid midfielders in the world. Yet the last few weeks that version of Tonali we saw earlier this season has been nowhere to be found. He’s loose with his passing, late with his tackling, and generally behind the play.

Tonali’s been booked in three of his last seven matches, and could be taken to task if Tottenham look to counter through the middle via Harry Kane, who can actually run a breakaway better than most strikers in the world.

AC Milan vs Tottenham prop bet

  • Pick: Dejan Kulusevski to assist a goal
  • Odds: +310 (BetMGM)

Tottenham playmaker Dejan Kulusevski has been the most consistent creative presence in the Spurs squad this season, if anyone on this team can claim any consistency at all. He’s delivering nearly 2.0 key passes a match, and his chances created are of very high value, registering at 0.14 xA per shot assist.

The Swedish international has a tough matchup here, going up against in-form tackler Lucas Hernandez, but the Milan wing-back plays so high at times that he could get caught out of position, which is where Kulusevski can pounce.

Kulusevski should have opportunities in this match to feed his Spurs teammates, or even get on the end of one, which happens less often. While selecting Kulusevski to score or assist feels more palatable, he’s more than twice as likely to assist as he is to score, and the odds double when picking him just to assist a goal. It’s worth the upgrade versus the risk.

AC Milan vs Tottenham live stream, TV channel

MORE: Watch Premier League matches live with fuboTV in USA

  TV channel Streaming
USA Paramount+, ViX, VIX+
Canada DAZN
UK BT Sport 1 BT Sport app
Australia Stan Sport
New Zealand Sky Sport beIN Sports beIN Sports Connect
India Sony Ten 1 Sony LIV, JioTV
Hong Kong beIN Sports 4 beIN Sports Connect
Malaysia beIN Sports Connect, sooka
Singapore beIN Sports Connect, StarHub TV+


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