UFC 299 is set to be an exceptional event! With a fight card full of household names, you’ll want to tune in - and we imagine you'll want to place a wager or two as well!

Below are my UFC predictions and betting picks for this Saturday's card. While the event is actually headlined by Sean O’Malley vs. Marlon Vera in their rematch bout, my UFC 299 best bets actually focus on some of the other fights instead. 

What can I say? You shouldn't bet on everything - you should bet where you see betting value!

Let's get in to my full UFC 299 predictions and best bets.

UFC Predictions & Betting Picks: UFC 299, O'Malley vs. Vera 2

All odds are courtesy of BetMGM Sportsbook unless otherwise stated.

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UFC 299 Prediction: Dustin Poirier vs. Benoit St. Denis - Poirier ML (+170)

Poirier opened as a small favorite and the line has completely swung towards St. Denis but I’m not expecting this to get any higher. Poirier is clearly towards the end of his career, but he’s been a staple in the Top 5 of the division for years.

Meanwhile, St. Denis only has one fight against a borderline top 15 opponent. Poirier is the more technical striker and has the cardio to go 5 rounds if he needs to while I’m not sure if St. Denis has the ability to go to war for 25 minutes.

UFC 299 Prediction: Petr Yan vs. Song Yadong - Yan ML(-125)

Yan has shown he can strike with the best in the division two fights back against O’Malley (he should have won that fight), and there isn’t much of a threat in Song shooting any takedowns. Yan has the striking advantage; he has the wrestling advantage if he wants to use it as well.

Yadong has quality wins, but this is a major jump up in competition for him. I would personally line this fight closer to Yan -180.

 

UFC 299 Prediction: Burns vs. Jack Della Maddalena - Burns ML (+140)

This is another fight on the card where the young fighter is taking on the veteran who has been at the top of the division for years. Burns has much better wrestling and I expect him to go to use it here. 

JDM has been taken down in the past by lesser fighters who didn’t know how to really control the position. It feels to me that if Burns gets on top in a round, he isn’t going to lose that round. Burns has power on his feet, but he isn’t going to be as technical as JDM, so he should look to avoid it and take this to the ground.

UFC 299 Parlay: Despaigne ML (-340) + Holland ML (-136) (+124 parlay odds)

Despaigne is an Olympic Taekwondo medalist making his UFC debut. He has run through 3 of his 4 opponents in under 15 seconds so he has a ton of power. 

Holland faces an opponent similar to himself in Michael Page, but Page is making his UFC debut at 37 years old, and Holland is just going to be able to outwork him on the feet for 15 minutes. 

It’s not insane odds, but these are two single bets that I personally don’t see losing.

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UFC 299 Best Bet At Long Odds: Curtis Blaydes vs. Jailton Almeida - Blaydes by Dec. (+350)

This fight is priced very close, but I think it plays out in a way that makes one of these fighters look like they should have been -300. Blaydes has a huge weight advantage over Almeida so I’m banking on him to be able to land takedowns and hold Almeida down for long stretches of time.

Almeida has been able to dominate all of his fights with wrestling, but we haven’t seen him have to fight defensively yet so I’m taking a shot on Blaydes winning. I think Almeida is good enough to make it to the final bell so I’m taking a long shot on Blaydes by decision.

 

Have questions or want other UFC 299 predictions, tips and picks? Feel free to reach out to me in discord or on Twitter at @MikeIannoneDFS. I'll share any last-minute betting updates from these accounts, too.

Good luck!