UFC 299 Gambling Preview: Can Chito Vera upset Sean O’Malley to claim bantamweight gold?

Whoo, boy! Now this is what I’m talking about.

UFC 299 is one of the most insanely stacked cards in recent memory, and so given that, we’re going to do things a little bit differently this week. We have 14 fights and I’m dropping 14 bets, one for each of them, because for a card this good, you have to celebrate. So let’s get to it.

As always, all odds are courtesy of our friends at DraftKings Sportsbook.

Photo by Jeff Bottari/Zuffa LLC via Getty Images

Straight Bets
Marlon Vera, +220

I wrote a full breakdown on this fight, so go check that out on Saturday morning, but the short version is this is a value play. I won’t be shocked if O’Malley leg kicks and moves his way to a decision (a la Conor McGregor in the Nate Diaz rematch), but there’s equally as good of a chance that he simply cannot hurt Chito, and he gets caught as he slows down. I’m taking the value on Chito.

Dustin Poirier, +170

This is another value play. Benoit Saint Denis is hell on wheels, but he has an open disregard for defense on the feet. That’s Poirier’s specialty, and in the striking, I think he has a clear edge. The question is in the grappling, as that’s always been a way to attack Poirier, but “The Diamond” is still no pushover and his wealth of experience should give him an edge in this five-round fight. Now, if Poirier’s chin is gone, this is going to all be moot, but I’m banking on him still having plenty of juice left in the tank.

Michael “Venom” Page, +110

In the featured fight of the main card, Page takes on Kevin Holland, and I have to say, this is one of my favorite bets of the evening. Much has been made about Page’s career and the fact that he mostly fought cans, and that’s absolutely true, but he also crushed those cans, which is what you want to see. The truth is, Page is a very talented fighter whose career has not been managed well, but that’s not a knock on what he can do in the cage. And what he can do lines up very well against Kevin Holland, who has not exactly been lights out. Recently, we saw Holland get tuned up by Stephen Thompson, and while Page is not as dangerous on the feet as “Wonderboy,” he’s a better defensive wrestler and still dangerous enough.

Petr Yan, -125

In the main card opener, Yan takes on Song Yadong in one of the best fights of the weekend. Not too long ago, people thought Yan would be the next great UFC champion and pound-for-pound fighter. Look how far we done fell. That being said, this is a good chance to get back on track. Song is a touch faster and constantly improving, but Yan has better timing and the ability to mix in takedowns.

This is do or die for Yan, who is on a three-fight losing streak and at risk of having a catastrophic career collapse. I think he wins it, and while most likely he’s doing it by decision (given how durable Song is), +140 is barely a difference and so just take him straight instead to cover your bases.

Curtis Blaydes, -110

I’ve been riding the “Curtis Blaydes is a future champion” bandwagon for so long at this point that getting off seems impossible. And while I don’t exactly believe he’ll be champion anymore, he should beat Jailton Almeida.

Blaydes keeps losing fights because he wants to show he can box but he doesn’t have a great chin. That’s not an issue with Almeida, who just wants to take him down. Given Blaydes’ physicality and wrestling background, that should be a tall task, and “Razor” should finally get a chance to let his hands shine.

Maycee Barber, -205

I probably wouldn’t bet this one if I wasn’t trying to put bets down on everything this weekend, but it’s fine. Katlyn Cerminara (neé Chookagian) hasn’t fought in almost 18 months and was already on the decline before that. Barber isn’t as good as she thinks she is, but she’s still improving and the athleticism alone should get her hand raised.

Pedro Munhoz, +190

Kyler Phillips is a hard guy to get a read on as he’s not the most active fighter, but what we see is usually pretty good. That being said, Munhoz has made a career out of winning this exact fight with veteran savvy and well-rounded skills. This is a 50/50 fight, but you’re getting a great price on Munhoz.

Ion Cutelaba, -120

Ion Cutelaba ran over Tanner Boser his last time out. Philipe Lins was run over by Boser. MMAth never tells the whole story, but it’s a pretty good shortcut in fights like this.

Joanne Wood +195

This is Wood’s final fight, and while she already lost to Maryna Moroz once (years ago) and she hasn’t looked good in ages, let’s start Saturday off with a sentimental bet and the hope that we keep 2023’s energy of feel-good retirement stories going.

Photo by Chris Unger/Zuffa LLC via Getty Images

Prop Bets
Jack Della Maddalena To Win By Decision, +300

I was so close to betting Gilbert Burns to pull off the upset here.

The hype is starting to cool on JDM and it’s easy to see why: After barnstorming early in his UFC run, his past two fights have been uninspiring split decision wins. That’s to be expected though as a young fighter rises through the ranks and becomes more well known, but now he’s getting a major leap up in competition.

Burns is a fighter I have perpetually underrated since his move up to welterweight, and I guess I’m going to do so again. He’s 37 years old and clearly slowing down. JDM should be able to keep this standing and box him up, but Burns is still very tough so I’m thinking it’s a third straight decision for the Aussie.

Mateusz Gamrot To Win By Decision, -175

My actual favorite bet of the weekend. This is so simple that it feels criminal. Gamrot is a cardio-wrestling monster. Rafael dos Anjos is a future Hall of Famer who is well past his best days and was always susceptible to that sort of game. So 1 + 1 still equals 2. Gamrot is going to get 15 takedowns, do minimal damage, and win a 30-27 decision.

Michel Pereira vs. Michal Oleksiejczuk Under 1.5 Rounds, +154

If you’ve ever seen Oleksiejczuk fight, you know that this has a great shot at hitting. The Polish fighter is an absolute maniac, and while Pereira has moved away from the wildman style that made him beloved before joining the UFC, Pereira is still very much someone who can get-or-get-got with the best of them. Expect anarchy.

Robelis Despaigne vs. Josh Parisian Over 1.5 Rounds, +230

Despaigne is an Olympic bronze medalist karateka who has knocked out his past three MMA opponents in a combined 19 seconds. That doesn’t bode well for Parisian, who is not great, but you know what does? Those three fights represent 75 percent of Despaigne’s MMA career and they came against fighters who had never (or barely) competed. This is a big step up for Despaigne, and Parisian is the sort of guy tough enough not to get totally walked over, even if he doesn’t win.

Assu Almabayev vs. CJ Vergara Under 2.5 Rounds, -140

I wanted to bet Almabayev Inside The Distance, but DraftKings doesn’t have that up yet. Instead we’re backing this bet for Almabayev, who is an impressive fighter with great grappling skills, as he’s taking on a guy who will exchange on the ground and has been submitted before.

Wrap Up
We skipped last week for the gambling column because, well, it was a terrible card. This week is the exact opposite of that. So many bets down that it’s probably impossible to come out ahead, but let’s give it the old college try.

Also, not putting this in the main section because of timing, but I’m also on Anthony Joshua To Win By Decision at +380 and a pretty heavy position on Joshua straight at -300.

Until next week, enjoy the fights, good luck, and gamble responsibly!

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