The UEFA Champions League round of 16 begins this week with eight two-leg matchups between some of the best teams in Europe.

Manchester City, Bayern Munich, PSG and Liverpool top the list of contenders for the Champions League, with the first two matches beginning on Tuesday. AC Milan takes on Tottenham and PSG will face Bayern Munich.

With all that in mind, let’s get to this week’s games. As always, remember that these bets are for regulation only.

Odds courtesy of Caesars Sportsbook.


AC Milan v. Tottenham Hotspur (+175), Draw (+255)

AC Milan couldn’t beat Chelsea in their two group stage matches and now they face a Tottenham side that not only won their Champions League group, but entered this past weekend nine points better than Chelsea in the Premier League standings. Is there any reason to think the Italian side fares better against this opponent?

Paul Carr: Milan generated very little against Chelsea, totaling 11 shots and 0.8 expected goals in the two games, and they’ve been in dreadful Serie A lately, winning once in the past six games. Tottenham are facing a midfield crisis with Rodrigo Betancur and Yves Bissouma injured and Pierre-Emile Hojbjerg suspended. Neither team’s attack has looked good over the past month. Milan have 3.0 expected goals over the past four games, and Tottenham haven’t done much aside from Harry Kane. Both teams will likely be content with a draw or even a 1-0 loss in this first leg, so I’m taking under 2.5 goals at -125.

Dan Thomas: Both teams come into this game in somewhat underwhelming form. Milan have had a shocker so far in 2023 and Spurs were horrendous against Leicester. I think is going to be a low scoring affair so take the under in Total goals.

Paris Saint-Germain (+170) vs. Bayern Munich (+140), Draw (+270)

PSG struggled a bit early on before finding their form while Bayern finished the group stage without a loss and a +16 goal differential. But can you really go against the squad that has Neymar and Kylian Mbappe?

Carr: I can, with Mbappe likely starting on the bench and Messi returning from injury. Bayern have been doing the usual Bayern things in Bundesliga, going unbeaten in 13 straight games and scoring multiple goals in 11 of them. The addition of Joao Cancelo also gives Bayern another versatile attacking piece, and PSG’s defense hasn’t been tight, with one clean sheet in eight league games since the break.

Given the question marks around PSG, the range of outcomes is wide. I simply trust Bayern more, and I’ll take them to win outright.

Thomas. Oh yes, I can go against them for sure. PSG are a mess at the moment. Even if Mbappe and Messi are fit there is absolutely no cohesion to the side. Bayern are getting better by the game. So I fancy the Germans to go to Paris and break some hearts on Valentine’s Day and get the win.


Borussia Dortmund (+155) vs. Chelsea (+175), Draw (+225)

Dortmund limps into the round of 16 after three consecutive draws to close out group play. Meanwhile, this Chelsea squad was very active in the latest transfer window and bear little resemblance to the side that won their group. Can we count on the Blues to get their act together?

Carr: Chelsea have drawn three straight games while scoring a total of one goal, but the attack seems to be coming around, with over four expected goals in those games. They’ll face a Dortmund side that has scored 15 goals in winning five straight league games yet remains vulnerable on the counterattack. Chelsea’s new signings should take advantage of that space, and I expect this to be a typically open Dortmund type of match. I’m taking a good price on over 2.5 goals (-105).

Thomas: Chelsea can’t score goals, and I’m not sure if you’ve heard, but that is rather important. Dortmund have been brilliant in 2023 and I can think they can get it done on Wednesday. I’m going for Dortmund to win.

Club Brugge (+275) vs. Benfica (-102), Draw (+245)

Benfica went unbeaten in the group stage, while Club Brugge finished second in their group behind Porto. Benfica scored more than twice as many goals in the group stage, but the Belgian side conceded only four goals in their run-up to this matchup. Is it offense or defense that takes this one?

Carr: I’m going with the offense and Benfica to win. They’ve been rolling in Portugal, sitting in first place with four straight shutout wins and one loss all season, and they were the best team in a UCL group that included PSG and Juventus. They won’t be the same without Enzo Fernandez, but Joao Mario and company should have enough to win in Belgium against Scott Parker’s side that has one win in seven games this year.

Former ESPN senior researcher Paul Carr is director of content for TruMedia.

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