UFC 299 Preview, PPV Main Card Predictions

UFC bantamweight champion Sean O’Malley is defending his 135-pound title in a five-round rematch against bitter rival Marlon Vera … which would have sounded strange a couple of years ago but alas; here we are just a few hours ahead of the UFC 299 pay-per-view (PPV) event. Dustin Poirier will collide with lightweight sensation Benoit Saint Denis in the UFC 299 co-main event, taking place at Kaseya Center in Miami, Fla., with some other familiar faces joining the lineup, as well. It’s also worth mentioning that Michael Page will finally get the opportunity to prove he was more than just a big fish in a small Bellator pond against a very tough out in the form of welterweight “Trailblazer” Kevin Holland.

Before we break down the five-fight PPV main card, which also features an important bantamweight battle between former champion Petr Yan and fan favorite Song Yadong, be sure to take a closer look at our comprehensive preview and predictions for this weekend’s preliminary undercard action on ESPN and ESPN+ by clicking here and here. The latest UFC 299 odds and a complete betting guide for the entire “O’Malley vs. Vera” PPV lineup can be located here.

Let’s take a look at what the main card has in store for us tonight in “The Sunshine State.”

135 lbs.: UFC Bantamweight champion “Suga” Sean O’Malley (17-1, 1 NC) vs. Marlon “Chito” Vera (23-8-1)

Sean O’Malley is bantamweight champion and the growing consensus seems to be that “Suga” is merely keeping the belt warm until the promotion grants wrestling “Machine,” Merab Dvalishvili, a shot at the 135-pound title. It’s hard to know at this juncture what O’Malley’s legacy will be as champion because of his bizarre path to the title. If you include his “Contender Series” destruction of Alfred Khashakyan back in summer 2017, “Suga” has 10 wins inside the Octagon and eight of those opponents are no longer competing under the UFC banner. The two wins he does have over active competition are big ones, edging out former champion Petr Yan at UFC 280 before stopping Aljamain Sterling at UFC 292.

The big talking point ahead of his Marlon Vera rematch is the outcome of their first fight. O’Malley fans will attribute the UFC 252 loss to injury; which is fine, but they conveniently leave out the fact that Vera’s leg kicks were a contributing factor. No question they’ll be on the menu tonight in “The Sunshine State” but my concern heading into UFC 299 is the challenger’s output, which seems to have dwindled over the last few years. I can also admit I wasn’t blown away by his decision victory over notoriously tough out Pedro Munhoz at UFC 292, which followed a decision loss to Cory Sandhagen at UFC San Antonio. Still, it feels like nitpicking when you look at his violent finish over Dominick Cruz at UFC San Diego, as well as his clinic against Rob Font at UFC Vegas 53.

What makes this fight so compelling is the fact that O’Malley has incredible one-punch power while Vera has a beard made of stone, competing in over 30 professional fights without ever getting finished. It’s been said that every fighter loses their chin if they stay in the game long enough, I just don’t know if this fight will be violent enough to test that theory. O’Malley is at his most dangerous when he’s playing matador, a strategy that will fail him at UFC 299 if Vera doesn’t take the bait. I know it sounds crazy to think two fighters with a combined 16 post-fight bonuses might turn in a boring match, but this could devolve into a 25-minute chess match with each combatant waiting for the other to make the first mistake.

I’ve never wanted to be so wrong in my life.

Prediction: O’Malley def. Vera by unanimous decision

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155 lbs.: Dustin “The Diamond” Poirier (29-8, 1 NC) vs. Benoit “God of War” Saint-Denis (13-1, 1 NC)

Dustin Poirier may not have the “BMF” title, but he should certainly be wearing the “MVP” belt. If you examine what “The Diamond” has done across his UFC career it’s nothing short of extraordinary. Forget wins and losses, just look at his level of competition — a veritable murderer’s row dating back to summer 2016. Not many lightweights in his position would risk their place in the division Top 5 by taking on a younger brute like Benoit Saint Denis but that’s what makes Poirier such a special athlete. That said, you have to wonder what the Louisianan has left in the tank after 15 years of back-and-forth violence. I don’t want to put him out to pasture because he was stopped by Justin Gaethje at UFC 291 because losing to “The Highlight” is nothing to be ashamed of. At the same time, Poirier turned 35 back in January and Father Time is undefeated. He’s also facing an all-action killer who at age 28, is competing in his athletic prime.

Saint Denis was a highly regarded prospect coming out of Brave Combat Federation in late 2021, though his Octagon debut against Elizeu Zaleski dos Santos left a lot to be desired (and marked the first loss of his professional career). Undaunted, the reinvigorated “God of War” came storming back with five straight wins, with all five ending by way of knockout or submission. That includes his “Performance of the Night” against Matt Frevola at UFC 295 last fall. The counterargument is that Saint Denis has not faced anyone in the division Top 10 and was able to rack up highlight-reel finishes against less than stellar competition. We also don’t know how well the Frenchman will hold up in a five-round fight in the off chance it lasts that long. The two times Poirier went all 25 minutes, he captured “Fight of the Night” honors against Max Holloway and Dan Hooker. Not surprisingly, pundits are leaning toward Saint Denis early and Poirier late.

This is a very difficult fight to predict because of the unknown. Poirier has been in countless wars in the past and won most of them, outboxing strikers like Conor McGregor and submitting wrestlers like Michael Chandler. This will not be new territory for him. At the same time, “The Diamond” will have to shine on defense and not allow himself to be dragged into the phone booth, where he remains most vulnerable against the taller and longer Saint Denis. Assuming that strategy comes to pass, it’s easy to envision the more experienced Poirier weathering an early storm, then settling down and taking over the bout after “God of War” blows his load and fades in the second half of the fight. It’s not a confident pick by any stretch of the imagination, but when push comes to shove, it’s hard to bet against the proven commodity, regardless of its wear and tear.

Prediction: Poirier def. Saint Denis by technical knockout

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170 lbs.: Kevin “Trailblazer” Holland (25-10, 1 NC) vs. Michael “Venom” Page (21-2)

Kevin Holland is an exceptional fighter who sometimes lets his jackassery get in the way of a serious run at the 170-pound title. That’s not entirely his fault, because it’s more important — financially speaking — to be a successful personality than it is a successful fighter. It’s also a lot easier, so sometimes it pays to just do enough to not get killed inside the cage. Some of the previews of this fight have drawn comparisons to the Stephen Thompson loss. Like “Wonderboy,” Michael Page is a rangy striker who presents a unique set of problems on the feet. That said, we can’t overlook the fact that “Trailblazer” broke his hand early in the Thompson fight and was basically a sitting duck until a merciful, fourth-round corner stoppage. What followed were back-to-back wins — and back-to-back finishes — over veteran bruisers Santiago Ponzinibbio and Michael Chiesa, later spoiled by a loss to welterweight wunderkind Jack Della Maddalena. I don’t think anyone will ever mistake Holland for being a wrestler but he’s been able to rattle off a couple of offensive takedowns when the occasion calls for it — and it just might against Page.

“Venom” was one of the must-see attractions in Bellator and built up a reputation for delivering highlight reel knockouts (get a sample here). I have a pretty strong stomach after covering this sport for nearly 20 years but what he did to the skull of Evangelista Santos remains uncomfortable to watch. It’s been said the Englishman was the best striker not signed to UFC and he certainly looked the part … though he had a little help from the promotion. Is anyone breaking out the good champagne for stoppages over Charlie Ontiveros and Charlie Ontiveros? Combined, they’ve been knocked out 16 times in MMA. It’s also worth noting that Page looks mortal when opponents don’t play his game. Decisions against Logan Storley (L) and Douglas Lima (W) come to mind. “Venom” is also turning 37 next month and will be dealing with a younger opponent who has a longer reach. Personally, I would have liked to see Page get a tune-up fight before getting thrown into the PPV shark tank, because I think Holland presents a unique (and difficult) challenge.

Page is a former kickboxing champion and will probably look like one this weekend in Miami. As for Holland, his awkward style and penchant for showmanship may make him a difficult target. I also think he’s going to use his in-cage antics as bait and let an overconfident Page get too close for comfort, resulting in a surprise submission that “Venom” won’t see coming until its already too late.

Prediction: Holland def. Page by submission

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170 lbs.: Gilbert Burns (22-6) vs. Jack Della Maddalena (16-2)

Gilbert Burns has managed to hang around the Top 5 of the division for the last few years but hasn’t really looked like a Top 5 fighter. The Brazilian was able to score a 170-pound title shot by knocking around a 42 year-old Demian Maia, which preceded a decision victory over a washed Tyron Woodley. Burns went on to get knocked out by Kamaru Usman in early 2021 and in the years that followed, compiled a 3-2 record with his lone finish coming against Neil Magny at UFC 283. Burns turns 38 in July and is clearly on the back nine of his combat sports career and UFC 299 marks the first time “Durinho” will fight an opponent under 30 since his submission win over Mike Davis at UFC Ft. Lauderdale back in early 2019. Wrestling is clearly his bread-and-butter and carves a path for his top-shelf submission game, though his striking leaves a lot to be desired. Burns does have power, he just lacks the fundamentals to set it up effectively. When you combine his age with the injury he suffered against Belal Muhammad early last year, it’s hard to feel good about his chances in this fight.

That’s assuming Jack Della Maddalena is the talent we think he is, based on what we’ve seen thus far in his UFC career. There’s also the very real possibility that he’s just a tornado of violence who is likely to get exposed when facing the experience and composure of combatants nestled in the upper echelon of the division. Maddalena made a name for himself on Dana White’s “Contender Series” back in late 2021 and has since compiled six straight wins, though his last two were not the lights-out finishes fans have become accustomed to. I’m not going crazy over his performance against Bassil Hafez last July, because the Aussie was tasked with fighting a short-notice opponent he didn’t train for and knew nothing about. That bewilderment became obvious during multiple grappling exchanges that had fans cursing the injury bug. The follow up to that win was another tough outing against Kevin Holland, which had some pundits casting doubt on Maddalena’s future, but I saw it the other way: he faced a Top 15 fighter and proved he had the mettle to get it done.

Burns will try to exploit Maddalena’s takedown defense and for good reason. His success in that department will likely dictate the outcome of this fight. If Burns does not succeed in grounding his Australian foe, he’s likely to get battered from pillar to post. Maddalena has better hands and more importantly, produces more volume. That’s a critical component in a three-round contest, which could mirror the Khamzat Chimaev fight in terms of insane, back-and-forth action. Expect this to be in the running for “Fight of the Night” and my apologies to all the “Durinho” fans, but I think this is Maddalena’s coming out party.

Prediction: Maddalena def. Burns by technical knockout

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135 lbs.: Petr “No Mercy” Yan (16-5) vs. Yadong “Kung Fu Kid” Song (21-7-1, 1 NC)

Less than two years ago, Petr Yan was ranked No. 1 in the bantamweight division and among the Top 10 in the pound-for-pound rankings. These days, it seems like fickle fight fans are ready to wipe “No Mercy” from the list of eligible contenders based on his recent performances. True, Yan has dropped three straight, but his opponents were current bantamweight champion Sean O’Malley, No. 1-ranked title contender Merab Dvalishvili, and former 135-pound titleholder Aljamain Sterling. There’s no disputing the loss to Dvalishvili but you can make arguments than Yan won his split decisions against O’Malley and Sterling. Of the 26 media outlets who scored UFC 280, only one scorecard landed in favor of “Suga.” Part of the issue for Yan, also apparent in his victory over Cory Sandhagen, is how long it takes for the Russian bruiser to get out of first gear. He’s an exceptional striker with a formidable wrestling base but sometimes seems content to do … nothing. Other times it looks as though Yan is mailing it in or attending a timeshare seminar. If he’s checked out for his UFC 299 return, or spends the first round trying to figure things out, “No Mercy” could find himself in big trouble.

Song Yadong is just 26 years old but already has 30 professional fights, which is both impressive and concerning. The “Kung Fu Kid” has been a fantastic addition to the bantamweight division with his all-action style, good enough for six post-fight performance bonuses, including one “Fight of the Night” opposite Marlon Vera at UFC Jacksonville. Cory Sandhagen showed that Yadong still has room to grow (har har) but again, at just 26 years old, the Chinese prospect has yet to reach his competitive prime. You wouldn’t know it by his output, which comes with devastating power, often at the expense of technique. That could be the deciding factor against Yan, who may present a broader palette to work from, in terms of the standup. The bigger concern is how Yadong will deal with the wrestling, having already been grounded en route to a decision loss to Kyler Phillips. Again, that all depends on how aggressive Yan wants to be with just 15 minutes to work. With a deeper toolbox and a more decorated resume, Yan feels like the right pick. Don’t expect it to come easy and we cold have an early contender for “Fight of the Night,” as well as another close decision for fans to argue about over the next few days.

Prediction: Yan def. Yadong by decision

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MMAmania.com will deliver LIVE round-by-round, blow-by-blow coverage of the entire UFC 299 fight card right RIGHT HERE, starting with the early ESPN+ “Prelims” matches at 6 p.m. ET, followed by the remaining undercard balance on ESPN/ESPN+ at 8 p.m. ET, before the PPV main card start time at 10 p.m. ET on ESPN+ PPV.

To check out the latest and greatest UFC 299: “O’Malley vs. Vera” news and notes be sure to hit up our comprehensive event archive right here. For the updated and finalized UFC 299 fight card and ESPN+ lineup click here.