UFC 299 Predictions: Bleacher Report Main Card Staff Picks

UFC 299 is set for this Saturday in Miami, and it will surely go down as one of the best cards of the year. It is absolutely stacked from top to bottom—so much so that some feel it will outshine the landmark UFC 300 card next month.

The headlining attraction will see bantamweight champion Sean O'Malley attempt the first title defense of his reign opposite a fellow fan favorite in Marlon "Chito" Vera. O'Malley is a big favorite to retain the title, but Chito is behind the lone loss of the champion's career—a first-round TKO in 2020—so there is plenty of intrigue attached to this one.

In the co-main event, lightweight legend Dustin Poirier will step into the Octagon for what could be the last time, taking on surging French contender Benoit Saint-Denis. While Poirier remains one of the top lightweights on the planet, he was brutally knocked out by Justin Gaethje in his last fight, while his French adversary has won five straight bouts, including a recent head-kick KO of Matt Frevola.

Before Poirier and Saint-Denis get to work, we'll be treated by back-to-back welterweight fights. First up, human highlight reel Kevin Holland will welcome former Bellator star Michael "Venom" Page to the UFC. Both men rank among the flashiest finishers in the division, so the odds of something crazy happening in this one seem high.

After that, former title challenger Gilbert Burns will look to slow the rise of Australian knockout artist Jack Della Maddalena in a fight that will push the winner right into title contention.

As if all of that weren't enough to encourage fans to buy the pay-per-view, the main card will be kicked off by a bantamweight fight between dynamic contenders Petr Yan and Song Yadong, who have exchanged plenty of trash talk in the lead-up. Like Burns and Della Maddalena at welterweight, the winner of this one will be right on the edge of title contention.

Every fight on the UFC 299 main card could seemingly go either way, and in dramatic fashion.

Scroll on to see how the B/R combat sports squad sees the pay-per-view unfolding in Miami.

Haris Kruskic: I'm mature enough to admit I've picked against Sean O'Malley in each of his last two fights and ate crow for it. Not again.

Yes, Marlon Vera is O'Malley's lone loss. But the champion has greatly improved since their first encounter. Also consider that Vera is historically a slow starter in five-round fights, and it could be enough for O'Malley to out-point the challenger.

Don't expect a knockout, though. Vera has never been finished in his 14-year career.

Prediction: O'Malley by split decision

Tom Taylor: Like Haris, I have long counted myself among O'Malley's doubters. However, after watching him knock out Aljamain Sterling to win the title, I have finally boarded the hype train—even if I just made it onto the caboose before it left town.

I also believe the champ will win this fight by decision, but it will probably be clear enough to warrant a unanimous call, rather than a split.

Having said that, I do see some paths to victory for Vera. He can have some success if he's able to attack the champion's legs again, particularly in the early going. I won't be shocked if he pulls it off, but I'm not picking against Suga anymore.

Prediction: O'Malley by unanimous decision

Lyle Fitzsimmons: I don't know if O'Malley was ready for Vera when they met in 2020, and I don't know if he'd have beaten him even without the sequence in which his calf was compromised and his foot injured.

But he's ready now.

Love his act or hate it, the guy is a government-grade sniper. He took out the best 135-pounder in the game the last time out, and Vera is not nearly as dangerous. He'll press the action, present an opening and pay the price. Game over.

Prediction: O'Malley by TKO, Round 1

Haris Kruskic: Sometimes the stage is just perfect for a changing of the guard.

Dustin Poirier has been close to the top of the lightweight division for nearly a decade, but it's been years since he fought new, hungry blood. Benoit Saint-Denis is scary. There's a reason the No. 12-ranked lightweight is getting a co-main event fight with Dustin freakin' Poirier. BSD can end things at a moment's notice.

Respect to Poirier for taking a fight like this that can only elevate his opponent, but it's the God of War's time.

Prediction: Saint-Denis by submission, Rd. 2

Tom Taylor: I count myself among Poirier's most ardent supporters. His fights are always thrilling, even when he comes up short, and he seems like a great dude outside the Octagon. I would love to see him snag the undisputed lightweight title before he calls it a career, but unfortunately, I just don't see it happening.

Saint-Denis is a juggernaut, and he doesn't seem like the type to be spooked by Poirier's experience and accomplishments. I see him putting the pressure on the former interim champion early, and eating some shots in order to land a big one of his own sometime in Round 1 or 2.

From there, it's just a question of whether he finishes things off with another knockout, or his jiu jitsu, which is even more dangerous than his striking.

Like Haris said, there's a changing of the guard afoot. If you see my eyes welling up as it happens, rest assured it's just my seasonal allergies.

Prediction: Saint-Denis by TKO, Rd. 2

Lyle Fitzsimmons: I'm a Poirier guy. So, I don't want to believe it's over.

And perhaps I'm being too sentimental, but I don't believe it's going to be.

Though he's lost a couple of recent fights in devastating fashion, Poirier is still a fighter. He still arrives in shape. He's still fired up by the prospect of combat. And he's motivated by the fact that a No. 12 contender is a betting favorite against him.

There'll be an exchange. He'll win it.

Prediction: Poirier by TKO, Round 3

Haris Kruskic: Jack Della Maddalena hasn't looked very dominant after two straight split-decision wins over Kevin Holland and Bassil Hafez, but he's still a very promising 27-year-old contender who has an opportunity to catapult into the lightweight title picture.

I just can't pick against Gilbert Burns, who is far and away the best fighter JDM will have stepped into the cage with. He can throw many different things at the Aussie on the feet and ground. That diversity and experience just feels like the perfect combination to overwhelm Maddalena.

Prediction: Burns by unanimous decision

Tom Taylor: It's hard to argue with Haris on this one. I love watching JDM. He has some of the best hands in the division. However, he has looked quite beatable in his last two fights, narrowly skirting Holland and Hafez, and even in the latter stages of his career, Burns is vastly superior to either of those men.

If Burns decides to stand and trade with JDM, there's a good chance he'll hit the deck, but I think he's smart enough to take this fight to the ground, where he will be levels above his foe.

If that's the way things shake out, it won't be long before he's choking the Australian out.

Prediction: Burns by submission, Rd. 2

Lyle Fitzsimmons: How good is Della Maddalena? How much does Burns still resemble, well...Burns?

Those will be the determining questions Saturday night.

Della Maddalena's momentum has leveled out now that he's begun fighting better opposition, but he's still not lost in almost eight years. That's impressive regardless of foe. As for Burns, he's 3-2 since a blowout loss to Kamaru Usman in a title fight in 2021, retiring the bearded husk of Jorge Masvidal in his most recent trip to Miami last spring.

Though I can easily envision a scenario in which Burns, now 37, beats his 27-year-old counterpart on top-tier muscle memory, it's more likely to see a younger, hungrier man outwork and outland his past-prime litmus test in a star-making turn.

Della Maddalena by split decision

Haris Kruskic: Michael "Venom" Page makes his UFC debut after a 10-year spell with Bellator. I can't think of a better first opponent than Kevin Holland, who similarly to Page, is always down for a scrap.

It'll be interesting to see how Holland approaches this fight considering he fought a very similar style in Stephen Thompson not too long ago. Low-volume, movement-based opponents tend to give him fits.

Although this will be a razor-thin decision, I'll go with the newcomer to start off on the right foot.

Prediction: Page by split decision

Tom Taylor: Honestly, I would have preferred to see MVP make his UFC debut against Thompson, but this matchup with Holland is nearly as compelling. The big question is whether MVP's careful sharpshooting will be more effective than Holland's wild, unpredictable style.

It's definitely possible the debuting Brit wins a wide decision or lands something flashy of his own, but he is 36 and hasn't been very active, so I think the more likely outcome is that he's the one hitting the deck.

I see Holland landing something weird early—maybe an elbow or a knee, and Page heading back to the drawing board before picking up his first UFC win.

Prediction: Holland by KO, Rd. 1

Lyle Fitzsimmons: Suddenly, 2020 seems like a long time ago.

Back in those COVID-clouded days, Holland was the star of the social-distancing show with five victories in eight months that backed up an interesting persona and compelling style.

Since then, not so much. He's been a pedestrian 4-5 with a no-contest in 10 subsequent fights and is drifting into gatekeeper territory while being fed to guys like Khamzat Chimaev, Jack Della Maddalena and now Page, who arrives after a prodigious run on the Bellator tier.

It won't be a walkover, and remember Page has fought exactly 26 seconds since 2022, but this seems like too big a spot for the newcomer to fail.

Prediction: Page by unanimous decision

Haris Kruskic: This is a reminder that UFC 299 is an outstanding card. Petr Yan and Song Yadong could easily headline a Fight Night.

I'm going with Yan here. I don't love picking someone who has lost three in a row, but his last loss was to Merab Dvalishvili and the previous two were tight split-decision losses to Sean O'Malley and Aljamain Sterling. He's not dropping fights to scrubs.

As promising as I think Song is, his two UFC losses came against high-volume strikers in Cory Sandhagen and Kyler Phillips. That is not a good sign against a destructive force like Yan.

Prediction: Yan by unanimous decision

Tom Taylor: Motion seconded.

This is definitely going to be a competitive fight, but I also see Yan winning a decision.

The two bantamweights are pretty similar stylistically, with great boxing and solid grappling, but Yan is a former champion who has beaten some of the best fighters in the division, while Song has stumbled each time he's been faced with the cream of the crop.

I'm picturing a fun, fast-paced fight where both men land some nice shots, but Yan is the obvious winner after three rounds. A higher striking output and maybe a few takedowns will be more than enough to convince the judges.

Prediction: Yan by unanimous decision

Lyle Fitzsimmons: Considering how devastating he looked not all that long ago, it's hard to fathom that Yan has lost four of five fights in the last three years.

A closer look reveals a DQ and two debatable decisions among the three losses, with the lone remaining L coming against a guy who's won 10 in a row and is the division's top contender.

And that's simply better than what Yadong arrives with. Neither of his last two wins, against Chris Gutierrez and Ricky Simon, were transcendent in nature, and he was stopped by Sandhagen in the "Sandman's" first fight after losing four of five rounds to Yan less than a year earlier.

"No Mercy" gets back to his winning ways.

Prediction: Yan by unanimous decision