UFC 299 Props: 5 Juicy Picks and Predictions From the MMA Prop Squad (Saturday, March 9)

Welcome to the latest edition of MMA Prop Squad, in which we offer an array of UFC 299 prop bets with oversized odds for Saturday's pay-per-view event.

Each MMA Prop Squad installment features a handful of picks from our squad of prop-betting enthusiasts, who have tallied +19.6 units a +5.8% ROI per bet to date.

For UFC 299, our prop-betting enthusiasts have put together their picks and predictions with five juicy prop bets. Check them out below.

As with all betting endeavors, always wager within your means. That guidance is especially important when dealing with prop bets. Although the props often offer tantalizing odds, they also cash far less frequently than standard bet types. And be sure to shop around for the best price since prop odds can vary substantially depending on the sportsbook.

*UFC 299 matchup odds as of Saturday and via FanDuel. Bet on UFC 299 with our FanDuel promo code. 

Tony Sartori: Josh Parisian by KO (+500)

Contributor at The Action Network

Fighter walkouts: Approx. 6:40 p.m. ET

There is a likely banger in-store on UFC 299's early prelims with heavyweight prospect Robelis Despaigne (-375) making his UFC debut against veteran Josh Parisian (+300).

All the hype in the world is on Despaigne entering this matchup despite the fact that he has fought only four times professionally in MMA.

The reason he is getting a shot in the UFC despite a mere 4-0 record? All four of those wins came by first-round knockout, with three of those four KOs coming within the first 12 seconds of the fight. Yes, that is absolutely insane, and I am just as pumped for his debut as anyone else.

However, at what point does this hype go too far? I believe we have surpassed that point with a -330 betting line.

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Could he knock out Parisian within 15 seconds? Yes, and I wouldn't even be surprised.

At the same time, this is still a guy who has never fought in a promotion higher than Fury FC, and we have never seen what he looks like in the second round against a game opponent. Not only has Despaigne never fought in a big MMA promotion, but his four opponents possess a combined 1-4 professional record.

The hype for a UFC debutant who has never faced anyone accomplished in professional MMA across two lower-tier promotions has officially reached mind-boggling levels. Despaigne possesses a monster frame with the longest reach in the promotion while boasting starching power, so he can knock out anyone.

But he is also 35 (older than Parisian) and is going against a guy who has been fighting UFC-level heavyweights since 2020. Parisian also carries immense knockout power, with 11 of his 15 professional wins coming by that method.

So, with that power in mind, you're giving us Parisian by KO/TKO at +500 against a guy with four pro fights and opponents with a combined 1-4 professional record across two lower-tier promotions? I'm taking that line every day of the week.

The Pick: Josh Parisian by KO (+500 at FanDuel)

Billy Ward: Josh Parisian by Submission (+1300)

Staff Writer at The Action Network

Fighter walkouts: Approx. 6:40 p.m. ET

Josh Parisian (+300) welcomes Olympic bronze medalist in taekwondo Robelis Despaigne (-375) to the UFC octagon on Saturday night. There’s plenty of hype around Despaigne thanks to his impressive early results (4-0 with four knockouts, the last three taking a combined 19 seconds) and insane physical tools – his 87-inch reach is the longest in UFC history.

Early returns like that are both a blessing and a curse. On the one hand, “The Big Boy” (yes, that’s his actual nickname) obviously packs big power. However, we have no evidence of him doing anything else.

His four opponents were a combined 1-0 when they faced Despaigne, with limited or no amateur experience. They also all appeared to be primarily strikers – and thus unlikely to test Despaigne’s grappling ability.

I’m sticking with the pick I made in my earlier Despaigne vs. Parisian preview in which I broke down why we don’t see many taekwondo stylists in high-level MMA. Despaigne is the first Olympian of the sport to make it to the UFC, and other practitioners combined that art with a heavy emphasis on grappling.

Despaigne has not, as far as anyone can tell. Which could be an issue against Parisian, a brown belt in jiu-jitsu out of Scorpion Fighting Systems in Michigan, a camp known for its grappling prowess.

The likeliest outcome here is a quick Despaigne knockout, given his massive physical advantages in this matchup. But a submission for Parisian might be the easiest path to a victory for the underdog, given that we’ve zero tape on Despaigne doing any competitive grappling.

Considering the circumstances, +1300 is far too long, and it doesn’t make much sense for that to be his least likely win condition as the odds imply. I’d take this bet down to +1000, or 10-to-1 odds.

The Pick: Josh Parisian by Submission (+1300 at FanDuel)

Dann Stupp: Michal Oleksiejczuk in Round 1 (+550)

Senior Editor at Action Network

Fighter walkouts: Approx. 6:55 p.m. ET

For every UFC event, I like to target at least one "dog walker" bout. Those fights are likely to end extra early, giving me the opportunity to walk to my pooch Dakota and stretch my own legs during the downtime between fights.

Tonight at UFC 299, I'm hoping we can get Dakota settled and nice early with an early preliminary card bout between middleweights Michal Oleksiejczuk (+124) and Michel Pereira (-146).

I've already targeted Oleksiejczuk as one of my moneyline plays (follow me in the Action App). And as fight time approaches, I've kept coming back to the prop markets and round props looking to squeeze out additional value.

In this fight, I expect Oleksiejczuk to start strong and find a willing dance partner in Pereira.

But former 205-pounder Oleksiejczuk should have a size and strength advantage over former 170-pounder Pereira. And I don't expect either one to care much about cardio or conserving energy for later in the fight.

When Dakota and I hit the mean streets of Lexington, Virginia, we occasionally run across a pair of rough-and-tumble alley cats who patrol the outskirts of the neighborhood. It takes little more than a "hello" or a snap of a twig for those two hellions to turn on each other and start throwing paws while getting twisted into a frantic tornado of swipes and bites and scratches.

I expect Oleksiejczuk vs. Pereira to look pretty much the same – just with less meowing and a slightly bigger live crowd. And I think Oleksiejczuk can get the better of it and walk away with an opening-round win when the dust settles.

I liked this Round 1 prop bet at +500 odds, which can be found at FanDuel. But let's pick off the stray +550 line at Betway and try to score even bigger. (Wouldn't that be the cat's meow?)

The Pick: Michal Oleksiejczuk in Round 1 (+550 at Betway)

Clint MacLean: Song Yadong by KO (+500)

Contributor at The Action Network and host of the Die Hard MMA Podcast

Fighter walkouts: Approx. 10:05 p.m. ET

Petr Yan (-142) enters this UFC 299 main-card opener on a three-fight losing skid, and you have to wonder where his head is at.

Song Yadong (+120), meanwhile, is a young gun who just keeps getting better.

We have seen Yan in some real battles recently, and as durable as he has been his entire career, we have seen him hurt. Yan is notorious for giving away the early rounds in fights, and that has led him to lose some close split decisions.

With his back against the wall, I believe Yan might start a firefight earlier than usual on Saturday while looking for a win, and that could go poorly. Corey Sandhagen recently came out and said that Song is the hardest puncher he has ever been hit by.

If Yan goes blow for blow with this kid, I expect the power of Song to be on display.

The Pick: Song Yadong by KO (+500 at FanDuel)

Dan Tom: Jack Della Maddalena in Round 2 (+650)

Contributor at The Action Network and host of the Protect Ya' Neck podcast

Fighter walkouts: Approx. 10:25 p.m. ET

For this week's MMA Prop Squad submission, I decided to target a "hot round" in a main-card attraction between Jack Della Maddalena (-162) and Gilbert Burns (+136).

Although I don't disagree with the money coming in on the Della Maddalena side, this fight seems like it boils down to two most likely outcomes: Either Burns gets his man down to the ground for a submission win, or Della Maddalena can find a finish on the feet with his superior striking.

Given that this is arguably common knowledge, I think that Burns will elect to get to his A-game early and often – which is why I admittedly hedged this bet with a play on Burns to win by submission (that you can still find in the neighborhood of +380 at multiple shops).

That said, if Burns fails to put away the deceptively tough Della Maddalena, then I suspect that the Australian will be particularly live to find a finish in Round 2.

Between Maddalena training with Craig Jones ahead of this contest to the fact that people tend to blow the Bassil Hafez fight out of proportion without proper context, I believe that Della Maddalena getting a mid-fight finish is the more likely outcome.

The Pick: Jack Della Maddalena in Round 2 (+650 at FanDuel)