UFC 299, Random Land: 25 Storylines And Fun Facts

After a very forgettable show in UFC Vegas 87 (despite several insane highlights), Ultimate Fighting Championship (UFC) travels to Kaseya Center in Miami, Fla., this weekend (Sat., March 9, 2024) for UFC 299, its third pay-per-view (PPV) event of 2024.

In UFC 299’s main event, Sean O’Malley defends his Bantamweight belt for the first time against nemesis (and lone conqueror) Marlon “Chito” Vera, while No. 3-ranked Lightweight contender, Dustin Poirier, takes on red-hot surging French madman, Benoit Saint-Denis, in the PPV co-feature.

UFC 299 is perfectly crafted with fun fights top to bottom (full card here), so before it all goes down tomorrow evening, let’s check out some random storylines, tidbits, and statistics ahead of showtime …

Four Years In The Making

O’Malley and Vera run it back four years after their first fight at UFC 252 back in Aug. 2020, which “Chito” won via technical knockout after he damaged the lead leg of “Suga” (watch highlights). Since that fight, “Suga” has gone (or remained?) undefeated. Nevertheless, it is a rematch that was going to happen at some point, but the fact it is occurring for a title makes it that much sweeter.

Main Event(s)

UFC 299 marks O’Malley’s second main event (his second straight), while Vera is headlining his fourth card.

‘Magic City’

UFC returns to Miami just 13 months after bringing UFC 287 to the Kaseya Center. Interestingly enough, both UFC 287 and UFC 299 have rematches as main events. Indeed, UFC 287 saw Israel Adesanya get revenge on Alex Pereira and reclaim his Middleweight championship (watch highlights).

Big Step Up

Saint-Denis goes from crushing Matt Frevola (watch highlights) — who was ranked No. 14 at the time — to fighting a former interim Lightweight champion and current No. 3-seeded Octagon veteran … a gigantic step up in competition.

“God of War” has looked incredible since getting toppled in his UFC debut, going undefeated (5-0) and finishing all of his opponents within 10 minutes of the fight.

Lightweight Title Shot?

If Saint-Denis defeats Poirier impressively, can he fight Islam Makhachev for the Lightweight title? Stick with me here as I try to land this plane …

Makhachev has said he wants to fight in June, which is UFC 302 (Newark, N.J.) or UFC 303 (International Fight Week). If he does end up fighting in June, it will be two months after UFC 300, which features Arman Tsarukyan vs. Charles Oliveira (which was called a No. 1 contender fight) and Justin Gaethje vs. Max Holloway (Gaethje was promised a title fight, too). I highly doubt Gaethje will turn around quickly if he defeats Holloway, and it will be tricky for Tsarukyan/Oliveira to turnaround quick as well.

So, with that context, Saint-Denis could leapfrog everyone because timing is everything in MMA.

Back-to-Back ‘Diamond’

Poirier has never lost back-to-back fights in his entire career.

Poirer’s Pearl Anniversary

Poirier will be competing in his 30th UFC fight on Saturday, as well as his 30th professional win. His current record is 29-8. Oh, and he has never fought in Florida, the state in which he trains.

MVP!

After 19 fights with Bellator, Michael “Venom” Page will make his highly-anticipated Octagon debut on Saturday against No. 13-ranked Welterweight contender, Kevin Holland.

Page is coming off year-long layoff — almost one year to the day when he stopped Goiti Yamauchi with a nasty leg kick.

“MVP” holds a 75 percent finish rate with 12 knockouts and is one of the flashiest strikers in MMA.

Welcome To UFC!

While we’re talking about UFC rookies, one other fighter is making his official promotional debut, Robelis Despaigne (4-0), who takes on Josh Parisian on the “Prelims.” Despaigne is an absolute monster, standing 6’7” with the longest wingspan in UFC history. He holds a 100 percent finish rate with four first round knockouts, with his last three fights totaling a combined 19 seconds. Two of those knockouts were three seconds (watch highlights) and five seconds.

Top 5 Matchup

Gilbert Burns will put his No. 4 Welterweight ranking on the line against Jack Della Maddalena, who has been on a roll since being signed to UFC, going undefeated (6-0) with four first round knockouts. The 27-year-old Australian can throw his name in the 170-pound title talk and set himself up for a No. 1 contender matchup … if he wins.

Back-to-Back ‘Durinho’

Just like fellow Octagon veteran Poirier, Burns has never lost back-to-back fights in his 28-fight professional career.

Do Or Die!

It is still insane to think about, but Petr Yan has lost three straight and four of his last five fights especially because of how dominant he was. The former Bantamweight champion is coming off year-long layoff, which was his own choice.

While he is still ranked No. 4 in the Bantamweight division, a loss to Song Yadong would be devastating for reclaiming his Bantamweight division.

His opponent is coming off two main event wins.

Heavyweight Rebooking

Curtis Blaydes and Jailton Almeida will finally clash at UFC 299 after their initial pairing at UFC Sao Paulo fell through because of a Blaydes injury … and the stakes are high.

With a win, Almeida could earn a shot at interim Heavyweight gold against Tom Aspinall, who is just waiting for a name. Almeida vs. Aspinall to headline UFC 301 in Brazil?

Blaydes, on the other hand, is coming off a knockout loss to former title challenger, Sergei Pavlovich (watch highlights), but he does hold a “win” over Aspinall, so maybe UFC runs back that matchup.

Fighting For More

Katlyn Cerminara (formerly Chookagian) returns to action after a 17-month layoff. During UFC 299 media day, she revealed that during her lengthy layoff, she suffered multiple miscarriages and has returned to fighting to help take her mind off of her personal struggles.

Cerminara takes on Maycee Barber this weekend.

Going Going Back Back To Lightweight Lightweight

Rafael dos Anjos returns to Lightweight (again) after two fights at Welterweight, which is odd because back in Aug. 2023 before his fight with Vicente Luque, the Brazilian claimed he was never going to drop back to Lightweight (only if it was for a title fight or a “super” fight).

Spoiler alert: Mateusz Gamrot is not a super fight nor a title fight.

However, dos Anjos believes a win over Gamrot will put him right back in the Lightweight title picture so that’s the reason he dropped back down to 155 pounds.

RDA On Prelims?

Speaking of dos Anjos, he will be fighting on the “Prelims” for the first time since UFC on FOX 11: “Werdum vs. Browne” in April 2014 where he fought Khabib Nurmagomedov. Since then, he has been involved in main- or co-main events in 18 out of 20 outings.

Rebooked

Ion Cutelaba and Philipe Lins will throw down at UFC 299. The pair of Light Heavyweights were originally supposed to fight at UFC Vegas 80; however, Lins pulled out of the fight the night of the event.

Cuelaba was not happy about the fight cancelation.

Retirement Rematch?

Joanne Wood and Maryna Moroz will run it back nine years later. The pair of Flyweights fought in Poland at UFC Fight Night 64: “Gonzaga vs. Cro Cop 2” back in April 2015.

It was Moroz’s UFC debut, and Wood was a -700 favorite. Moroz pulled the big upset and submitted Wood in less than two minutes. Since their first fight, both women moved up to Flyweight and had ups and downs in their careers.

When the fight was announced, she teased retirement by writing on her Instagram: “Time to saddle up for one last go! Yeehaw.”

UFC 299 Fight Leader

The fighter with the most amount of fights on UFC 299 is dos Anjos (47).

UFC 299 Fight Rookie

The fighter with the least amount of fights on UFC 299 is Despaigne (four).

UFC 299 Knockout King

The fighters with the most amount of knockouts on UFC 299 are Poirier, Holland and Michal Oleksiejczuk (14).

UFC 299 Submission Savant

The fighter with the most amount of submissions on UFC 299 is Almeida (12).

Winners And Losers

Seventeen fighters are coming off wins, while nine are coming off losses.

Multi-Divisions

Here are the divisions that will be on display this Saturday:

• Two Heavyweight fights
• One Light Heavyweight fight
• One Middleweight fight
• Two Welterweight fights
• Two Lightweight fights
• Two Bantamweight fights
• One Flyweight fight
• Two women’s Flyweight fights

Beta Dog

According to DraftKings, UFC 299’s “biggest” underdog is C.J. Vergara at +425.

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Remember that MMAmania.com will deliver LIVE round-by-round, blow-by-blow coverage of the entire UFC 299 fight card right here, starting with the early ESPN+ “Prelims” matches online, which are scheduled to begin at 6 p.m. ET (simulcast on ESPN at 8 p.m. ET), before the pay-per-view (PPV) main card start time at 10 p.m. ET (also on ESPN+).

To check out the latest and greatest UFC 299: “O’Malley vs. Vera 2” news and notes be sure to hit up our comprehensive event archive right here.