UFC 299 predictions, best bets, odds: Sean O’Malley prop, Benoit Saint Denis among top picks to consider

On paper, UFC 299 on Saturday looks like one of the most competitive main cards in the last couple of years. The event is set to go down from the Kaseya Center in Miami and all five fights are fairly close in odds as people try to decipher who to place a wager on. 

O’Malley sees himself as a superstar in the making. Pomp and circumstance can take you far in the fight game but you need the record to back it up. O’Malley looked every bit the real deal by vanquishing former titleholder Aljamain Sterling. O’Malley can begin carving a true legacy for himself against a hungry field of bantamweight contenders. He’ll first have to avenge his 2020 loss to Vera, a violent and ultra-tough fighter who hasn’t been stopped in 32 professional fights.

After a rough start for our best bets coming in at 1-4 at UFC 297, we rebounded nicely with a 3-2 record at UFC 298 to bring our record to 4-6 on the year. We have attempted to identify the best plays for every main card fight on Saturday, looking to raise the year’s record above .500 by the time all the action has come to an end.

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Let’s take a look at our picks for the best bets for the UFC 299 main card.

Petr Yan vs. Song Yadong

Petr Yan moneyline (-115)

Yan enters this fight having lost four of his five most recent fights. At a surface level, that suggests Yan is done as a fighter at the elite level. Dig a little deeper and you see that those losses came against the best of the best in the bantamweight division with one coming via disqualification and two by split decision. Yan may have fallen out of the title picture, but there’s likely still plenty of gas in the tank and he should be motivated when he faces Yadong, whose style matches up nicely with what Yan does well. Yadong does have some good wins on his resume but also has lost to Kyler Phillips and Cory Sandhagen in the past few years. Rather than try to land on a method of victory, the play here is to just take the simple moneyline play for the more established fighter with more tools to win the fight.

Gilbert Burns vs. Jack Della Maddalena

Gilbert Burns moneyline (+140)

This fight is likely determined entirely by Burns’ willingness to work to put the fight on the floor. If Burns can get takedowns, Della Maddalena is likely sunk in such a big step-up fight. Della Maddalena was able to escape with a split decision over Bassil Hafez despite spending more than five minutes of the first two rounds under Hafez. Burns is a decorated and dangerous grappler and if Della Maddalena finds himself under Burns for any significant amount of time, he is likely not making it to the final bell. Alternatively, and despite having heavy hands, Burns can be busted up on the feet a bit and Della Maddalena has blistering boxing skills. I have to believe Burns’ team has him well aware of the importance of closing distance and getting the fight to the ground so it’s worth throwing a bit behind the small upset.

Kevin Holland vs. Michael Page

Fight to go the distance: No (+110)

These two fighters have a combined 72% of fights that have ended before the final bell. Add in the way their styles mesh and it seems a little silly that the fight not going the distance is sitting at plus money. This fight could end on the feet at at any moment, with either man landing a big shot or powerful flurry. Holland could also take the fight to the ground and find a submission — he has seven in his career — against Page, who has never really had to elevate his grappling game thanks to mostly favorable matchmaking in Bellator. Plus money for the fight to end before the finish of the third round is the kind of generous line you have to jump all over.

Dustin Poirier vs. Benoit Saint Denis

Benoit Saint Denis moneyline (-210)

Admittedly, it stings a little bit to go against Poirier, one of the easiest guys in the sport to root for over the past decade. But, as they say, styles make fights and this is not a favorable pairing for Poirier. The former interim champion’s takedown defense has never been all that solid, successfully defending takedowns at a rate of 63%. Saint Denis averages 4.55 takedowns per 15 minutes. There’s a clear path to victory for Saint Denis: Close the distance and put Poirier on his back. It’s a little too tricky to figure out if Saint Denis can score a submission or knockout for a bet on method of victory, so we’ll stick to the moneyline.

Sean O’Malley vs. Marlon Vera

Sean O’Malley via decision (+100)

Vera is a dangerous challenger, as made clear by defeating O’Malley in their first fight. But duplicating that success isn’t going to be easy, especially with O’Malley only gaining confidence of late and being the more dynamic fighter. Vera is incredibly durable, never having been stopped in his career. Considering all the factors heading in, it feels as though O’Malley is set up for a decision win. Vera gets hit with strikes at a higher rate than he lands but still manages to gut out every fight while O’Malley has never been five rounds in his career. It feels like the most likely result is the best play to make.

Who wins UFC 299: O’Malley vs. Vera 2, and how exactly does each fight end? Visit SportsLine now to get detailed picks on UFC 299, all from the MMA expert who profited more than $6,200, and find out.