PSG's Lionel Messi controls the ball during the group H Champions League soccer match between Maccabi Haifa and Paris Saint-Germain in Haifa, Israel, Wednesday, Sept. 14, 2022. (AP Photo/Ariel Schalit)

Champions League Round of 16 Preview

Following a nearly four-month-long break, the Champions League is back. The round of 16 kicks off today, with Tottenham heading to Milan and Bayern traveling to France tomorrow to kickstart the first leg.

Often times a clear favorite emerges from the crowd. Not this year. The Champions League often features juggernauts primed to make the deep run (cough, Madrid), but this truly is one of the few years where it’s anyone’s game.

AC Milan vs. Tottenham

Chelsea finished ahead of Milan in Group E despite a tumultuous first half to their season. Milan, fresh off of last year’s Scudetto, have been one of the most disappointing teams in European football this year. The Italian side currently sits fifth in Serie A, a full 18 points behind the juggernaut that is Napoli.

Milan suffered a horrific start to the New Year, with only eight points scored from their seven league matches since the World Cup break ended. A lot of this skid has to do with superstar goalkeeper Mike Maignan’s injury. Maignan hasn’t played since October after suffering a disrupted calf muscle. Backup keeper Ciprian Tatarusanu hasn’t exactly inspired in his place.

Similarly, English side Tottenham also disappointed at points this season. Tottenham barely won Group D, finishing only one point ahead of the incredibly disappointing side Eintracht Frankfurt.

This dismay has carried over into the Premier League. Like Milan, Tottenham sit fifth, two points behind Newcastle. A lot of this has to do with Tottenham’s lack of attack. Sure Harry Kane has scored 17 goals this season, but what’s the point if nobody else in the squad is scoring? Stars Son Heung-min and Dejan Kulusevski have combined for just six league goals this season. If you add big money signing Richarlison’s goal tally to that, you come out with a whopping six goals. Richarlison hit Puskas nominees at Qatar’s World Cup, but can’t score in the Premier League to save his life.

This one could go either way. A betting man takes Tottenham on goal differential.

PSG vs. Bayern Munich

The headline to this match is who isn’t playing: Kylian Mbappe and Lionel Messi. Paris potentially goes into this match without arguably the two best players in the world. Both players were named to manager Christophe Galtier’s squad despite originally being ruled out for the match. Whether they play is a completely different matter.

“Kylian trained with the squad today and completed the whole session,” said Galtier.

“I didn’t think he would be ready. We took the decision to let him take part if he felt ready. We’re not quite sure if he’ll be on the team sheet, we’ll see tomorrow morning.”

PSG looked lost without the legendary duo on Saturday. The French club lost 3-1 to rival Monaco. PSG looked useless throughout the match, and things can only get worse against Bayern Munich.

Expect Bayern to wallop PSG if Mbappe and Messi don’t play. The match could go either way if they do play.

Club Brugge vs. Benfica

Brugge, normally a contender in Belgium, currently sit fourth in the Jupiler Pro League. Despite the predicament, the Belgian side features a young and hungry squad. Ferran Jutglà, Andreas Olsen, and club stalwart Hans Vanaken have all enjoyed productive seasons thus far. We saw this hunger in group play. The side beat out Bayer Leverkusen and Atletico Madrid to finish second in Group B, finishing just one point behind FC Porto.

Benfica, on the other hand, means business. Every year a non-top-five league team makes a deep run in Champions League. My best guess is Benfica ends up as this year’s team.

Benfica sit atop Liga Portugal with a 5-point lead over Porto. The Portuguese side also shattered expectations in the group stage, winning a group that included PSG and Juventus.

Benfica should win this one easily.

Borussia Dortmund vs. Chelsea

Chelsea have been downright awful this season. The English club sits tenth in Premier League, with only 31 points from 22 league matches. Graham Potter has found himself on the hot seat despite reportedly having no expectations for this season. Owner Todd Boehly expected nothing and was still disappointed.

Chelsea spent over $200 million during January’s transfer window in a vain attempt to save their season. Based on recent performances, the treasure chest will sink with the ship.

Dortmund meanwhile are having one of the most Dortmund seasons to date. They sit third in Bundesliga and finished second in their group behind Manchester City. Pretty standard for Dortmund.

Graham Potter likely needs this win to keep his job.

Eintracht Frankfurt vs. Napoli

Napoli are a favorite team in this year’s Champions League. The Italian side is led by potent young poacher Victor Osimhen and prime Eden Hazard regen Khvicha Kvaratskhelia (gesundheit). The duo have combined for a whopping 38 goal contributions in Serie A this season.

Napoli plays some of the most creative soccer today. They emphasize the counterattack, with players that can cross the ball in from anywhere and dribble around anyone. You’d be hard-pressed to find a faster attack in European soccer.

That’s not to say they’re lacking defensively. South Korean star Kim Min-Jae rounds out a solid defensive line. Not only can Napoli run the score up on you, but they’ll never let you back in the game.

Frankfurt face the tough task of upsetting many fans’ Champions League favorite. Frankfurt are doing alright in Bundesliga this season, sitting in sixth place. They also barely escaped Group D, although it was a group of death. Napoli should take this match easily.

Liverpool vs. Real Madrid

A lot of what was said about Chelsea could be said about Liverpool, minus the potential coach firing. After all, how could you sack Jurgen Klopp?

Liverpool sit ninth in the Premier League, only one point ahead of Chelsea. This comes despite big money transfers like Cody Gakpo and Darwin Nunez joining the club. The Merseyside club have played an uninspiring brand of football, lacking on both ends of the pitch. Their only hope is to capitalize on Madrid’s injuries.

Madrid have been hit by the injury bug this season, particularly with reigning Balon D’Or winner Karim Benzema. By their standards Madrid have been lackluster this season, sitting second in La Liga. If Madrid can’t get an attack going, expect Liverpool to go all out and capitalize. After all, the English club has nothing to lose at this point.

RB Leipzig vs. Manchester City

It feels like this fixture happens every season. If there’s ever been a year for Leipzig to finally punch through City’s wall it’s now.

City have been lackluster this season. Despite Erling Haaland’s best efforts, Manchester have disappointed, sitting in second place in the Premier League. A recent shift to a 3-2-4-1 has overpowered opponents, but the change has left the club somewhat exposed defensively. This team can be beaten on the counter, and Leipzig could be the team to do it.

Leipzig have a pacy attack, with players like Timo Werner and Andre Silva able to get past opposing backlines. Star Christopher Nkunku is still out with an injury, which drastically hampers Leipzig’s chances. Expect City to win this one, but don’t be surprised if Leipzig is able to sneak a few goals in.

Inter Milan vs. FC Porto

A tale of second-place sides. Both teams finished second in their group and are second in their domestic leagues.

Inter are holding tight with 44 points from 22 matches. Normally this would be enough to at least be in the Serie A title race, but Napoli have run away with the Italian league. This shouldn’t be a knock on Inter, however. Inter still have one of the best midfields in European soccer. The club also features a potent striker in Lautaro Martinez.

This doesn’t mean that things will be easy for Milan. Port is a squad primed for a fight. The squad managed to win a group featuring Bayer Leverkusen and Atletico Madrid for one. They’re also still in spitting distance for the Liga Portugal title with over half a season to go. This is a squad with a few stars, like goalkeeper Diogo Costa.

Milan should take this one, but don’t be surprised if Porto pulls off the upset.

About Connor O'Bryan

Connor O'Bryan is a world soccer reporter for ESPN Gainesville. He also sometimes covers baseball and other sports. He has previously written for WUFT Gainesville and for Atrium Magazine. Connor also cohosts the "Off The Bar Podcast", a student driven podcast that focuses on the global soccer landscape.

Check Also

Inter Miami

Inter Miami Front Three All Score in Victory Over SKC

Inter Miami went on the road to Arrowhead Stadium to face Sporting Kansas City on …