Champions League Quarterfinal Best Bets For 4/18/23: Napoli vs. AC Milan, Chelsea vs. Real Madrid

The first legs of this batch of UCL Quarterfinals included big home wins from Milan and Madrid, the two most successful clubs in this competition. Now, both will be forced to close things out on the road against Napoli and Chelsea, respectively, in some matchups that are very familiar for both sides. Let’s take a look at the odds and make some picks for these decisive second legs.

Napoli vs. AC Milan

Not too long ago, many viewed this matchup as essentially over before it even began; the Rossoneri have not been in the strongest form domestically, while their domestic foes to the South have been tearing the league apart. But just before the first leg, Milan notched a dominant 4-0 victory, before of course going up 1-0 on aggregate in this tie at home.

It was a very evenly-fought match by almost every single metric, but the home side were ultimately the more opportunistic, and found the only goal of the match through a nice breaking team move finished off by Ismael Bennacer.

To make matters worse for Napoli, key midfielder Andre-Frank Zambo Anguissa picked up a second yellow card, and will thus be unavailable for the return leg. If there’s any solace they can take, it’s that they were able to avoid conceding a second goal or more while playing around 20 minutes with a man disadvantage.

This one’s incredibly hard to call; on one hand, Milan are in shaky form, but they’re a club that has plenty of European pedigree, has found a way to win huge matches in recent years, and more to the point, has owned Napoli over the past few weeks. As for the hosts, they don’t exactly have the best track record in Europe, to the point where they’re viewed by some as “cursed” in the competition.

The thing is, those Milan successes came with Napoli’s outstanding striker Victor Osimhen out with an injury. He’ll be back for this match, and just how ready he is to contribute (and for how long) will go an extremely long way towards finding a winner on Tuesday.

As for the moneyline, Napoli are -145, and I like that value. This is a tough team to beat once, let alone over and over, and it’s hard to imagine that Milan will keep them stifled for 270 consecutive minutes. If Osimhen is able to have any impact, he could turn the tides in a matchup that was extremely close even in his absence.
I’d also take the under for a line of 2.5 goals, which is just a bit worse than even money. Milan will play an extremely defensive style going on the road with a lead, and with Mike Maignan back in the net and in excellent form, it’s hard to imagine that going too poorly. Yes, I think Napoli should find a way through, but I’d be far from stunned if it was another 1-0 match. Conversely, an early goal from Milan could lead to a true turtle-esque approach that would not likely see multiple more goals scored

Lastly, the big pick; team to advance. Even if Napoli win small, and this heads to overtime, I’m a fan of their odds in what should be a pretty rowdy home atmosphere; in such a tight matchup, something as seemingly small as 30 extra minutes at your home pitch could truly be the game changer, so I’m picking the home side to move on to the UCL Semifinal.

Best Bets: Napoli ML (-145), u2.5 goals (-115), Napoli to Advance (+110)

Chelsea vs. Real Madrid

There’s pretty much no reason to sugarcoat it; Chelsea are in disarray. In their past five league matches, they’ve drawn twice and lost three, and not even against particularly good competition for the most part. They have not experienced the “new manager bounce” under caretaker Frank Lampard, and were thoroughly beaten in the first leg of this tie in Madrid.

Madrid are sitting in a great position. They’re up 2-0 after absolutely commanding the first leg, and as a bonus, Ben Chilwell even picked up a red card, so they won’t have to worry about him on Tuesday. While it was a frustrating for me after I tabbed Vinicius Jr. to score and he assisted twice instead, Madrid will be pleased to see the young Brazilian star continuing to perform well, and Karim Benzema putting a ball in the back of the net- that’s a winning combination in this competition.

The odds for this one are interesting; everyone expects Madrid to be in control, but they still have plus-odds on the moneyline because, well, it’s hard to pick a team to win when they know they don’t quite need to. That being said, I want to capitalize on the value and take them on the moneyline. The line between winning and not advancing at all is finer than it may appear, and nobody knows that better than Madrid, the kings of this competition.

Of course Los Blancos aren’t really in the best form of all time, as they’ve struggled in La Liga recently and really throughout the season. But if anything, the moot league season- top four is a lock, while the trophy is out of reach- further underscores just how much of a focus this competition is. There’s nothing to rest for, with the Copa del Rey final a couple weeks away. And even if there was, this is Madrid- the Champions League means everything to them.

Another UCL mainstay, along with Madrid team success, is Karim Benzema’s individual excellence. He hasn’t been up to the ridiculous standard he set a year ago, but he’s still one of the greatest European performers of all time, and is a scoring machine in UCL knockouts- in plus-odds, his anytime goalscorer prop is too good to ignore.

Best Bets: Madrid ML (+140), Benzema Anytime Goalscorer (+120)

From starting my own blog in Middle School, to working on a friend’s in college, and finally joining the Lineups team this year, I’ve been writing about sports for over a decade and betting on them as long as I’ve been legally able. I graduated from the University of Michigan last year, where I took sports journalism classes alongside my business major. Having played and watched sports for almost my whole life, I aim to provide insight and entertainment, as well as profitable picks, in my writing about professional and collegiate leagues.

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