Best Boxing Bets, Predictions & Picks: Usyk vs. Chisora, Davis vs. Santa Cruz, More (Saturday, Oct. 31)

This is a huge weekend for boxing bettors.

The boxing slate features two title fights and a potential heavyweight title eliminator that could reveal the next opponent for unified champion Anthony Joshua in 2021.

So, where’s the value? Our staff is here to break down their favorite boxing bets for Saturday's three matchups:

• Oleksandr Usyk vs. Dereck Chisora
• Naoya Inoue vs. Jason Moloney
• Gervonta Davis vs. Leo Santa Cruz

Odds as of Friday and via DraftKings. Get up to a $1,000 sign-up bonus at DraftKings today or see more offers and reviews for the best online sportsbooks.

Boxing Betting Picks

Raheem Palmer: Davis vs. Santa Cruz

When I’m handicapping fights, I like to take note of who is the clear A side in each match up. In this fight, it’s clearly Gervonta “Tank” Davis.

Floyd Mayweather Jr. was notorious for carefully choosing opponents during the second half of his career and we shouldn’t expect anything different from Davis, the most successful fighter under the Mayweather promotions banner.

On paper, the 32-year-old Leo Santa Cruz is a worthy opponent as he holds a 37-1-1 record with championships in four different weight classes. His only loss was in a majority decision to Carl Frampton and he quickly avenged his loss in a rematch. With Santa Cruz, we’re getting experience and a high work-rate, which seems ideal with a fighter who’s taller and holds a slight reach advantage (69 inches to 67.5 inches).

Nevertheless, Santa Cruz has just 19 knockouts in his 37 victories and is moving up from 126 to 130 for just his second fight in the weight class to fight a guy who’s clearly the bigger, stronger and harder puncher. Santa Cruz didn’t have pop at 126 and he certainly won’t have it at 130. Being a high-activity pressure fighter has its advantages, but what happens when your power can’t keep your heavy-hitting opponent honest?

At 25 years old, Davis is 23-0 with 22 wins by knockout — a KO rate of 95.5%. He’s not just beating tomato cans either; he has stopped Jose Pedraza, Liam Walsh and Francisco Fonseca, who were all undefeated at the time of their fights.

This fight feels reminiscent of Sugar Shane Mosley vs. Antonio Margarito, where you have a pressure fighter up against a younger, faster and more athletic boxer. Santa Cruz will try to come forward and he may certainly be the busier fighter for parts of this fight, but against one of the hardest punchers in boxing he’ll be playing with fire and eventually he’ll pay the price.

Of course, Davis’ struggles to make weight and problems outside of the ring have been well documented and did bring me pause initially. But he is a more focused fighter these days. Spending the past three months training in Las Vegas under the direction of Mayweather has worked wonders for him as he successfully made weight, coming in at 129.75 pounds.

Through 23 fights and seven years of his career, it’s clear the only thing that can stop Davis is himself. He appears to have moved past that. I think Davis lives up to his nickname as “Tank” and rolls over Santa Cruz on the way to a knockout. BetMGM currently has the best line on his knockout prop, but I would bet this to -110.

The Pick: Gervonta Davis by KO/TKO (+100)

[Bet Davis vs. Santa Cruz at BetMGM and get a $500 INSTANT deposit match]

Michael Leboff: Davis vs. Santa Cruz

Picking a winner and betting on a fighter are two very different things. The odds already tell you that Davis wins this fight more often than not (his odds translate to an 80% implied win probability). If you are betting Davis, whether that means roping him into a parlay or laying the wood or taking him in a prop, you need to know that you are paying a steep tax in a very tricky fight.

Floyd Mayweather is not shy about promoting Davis and that kind of hype does tend to inflate the odds in boxing matches. The 25-year-old Davis could be a star, but we’ve seen him turn in flat performances against lesser opposition. Tank’s power is still the most important tool in this matchup, but there are flaws to his game, most notably his stamina.

It’s pretty clear how Davis will want this fight to end. He’s a knockout artist and his clearest path to success is through a stoppage. But if he doesn’t get it, he’s in trouble — especially if Santa Cruz can bank a round or two in the early stages of the fight.

Santa Cruz’s biggest edge in this fight is his endurance and ability to maintain a ridiculous output deep into the championship rounds. In fact, I think he could be a great live betting option in the middle stages of the fight so long as he is hanging in there.

Tank is built to end fights early. Santa Cruz is built to win them late. It would not be surprising to see LSC take four of the last six rounds if this fight goes to the final bell. I think Santa Cruz has a good shot at pulling the upset relative to his odds, which imply he wins just 15.2% of the time. DraftKings currently has the best line on Santa Cruz and I'd bet him down to +400.

The Pick: Santa Cruz ML (+500)

[Bet Davis vs. Santa Cruz at DraftKings and get a $1,000 sign-up bonus.]

Malik Smith: Usyk vs. Chisora

Oleksandr Usyk is fighting his second career bout at heavyweight and his first wasn't much of a real test. After weighing in at just over 217 pounds, the former undisputed cruiserweight champion will be nearly 40 pounds lighter than his heavy-handed opponent Dereck Chisora.

Chisora is a true heavyweight bruiser and will test whether Usyk truly can compete in this division. In Usyk's last bout, he was described as the 200-pound Vasiliy Lomachenko — a nod to his fellow Ukrainian — and the label rings true when you watch him. He's crafty on his feet, quick with his hands and can frustrate just about anyone in the ring.

But it's much tougher doing that when a man like Chisora is standing in front of you pushing the pace. "War" Chisora is 36 years old and his past two fights could be a window into his approach — jump on the smaller fighter early and go for the quick kill. Usyk is likely aware of this potential strategy and should use those quick feet and 4-inch reach to keep his opponent at bay.

Chisora knows that's the only way he can win this fight, but I think he'll tire himself out early by going for a big swing. I don't expect Usyk to give Chisora that opportunity and instead will box on the outside and try to get a late finish.

I'm going to bet the fight doesn't go the distance, which allows for the Usyk to finish a tired Chisora, or for Chisora to land a surprising finish. BetMGM currently has the best line at -150.

The Pick: Fight Does Not Go the Distance (-150)

[Bet Usyk vs. Chisora at BetMGM and get a $500 INSTANT deposit match]

Smith: Inoue vs. Moloney

Inoue is the biggest favorite among the three big main events on Saturday's slate. His odds reflect the legend he has built over the years with his exciting style, but laying -1115 (91.7% implied odds) is clearly out of the question here. Even a win by knockout for “Monster” is listed at -335 (77% implied odds).

The odds that this fight goes the distance are listed at -455 for “No” and +300 for “Yes,” but the over/under on the round total is basically a coin flip. I think Moloney is being overlooked in a fight where expect him to be very competitive — at least up to the 10th round.

I’m not sure he has enough in his tank to withstand the kind of flurry that almost finished Donaire, but the Australian is crafty enough to make it through the seventh. I’ll take the over and sweat this one out with Jason’s twin brother Andrew.

The Pick: Over 6.5 (-106)

[Bet Inoue vs. Moloney at DraftKings and get a $1,000 sign-up bonus.]