UFC & MMA Betting

UFC 299 Fight Card and Predictions: Could It Be Better Than UFC 300?

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The biggest MMA promotion returns to Miami with a spectacular event and a UFC 299 fight card that makes our heads spin. Sean O'Malley will attempt his first title defense in the main event but he is far from the biggest name on that card, if you ask us. Check out the full card and our UFC 299 predictions.

UFC 299 Fight Card: Everything You Need to Know + UFC 299 Predictions

Sean O'Malley may think he is a superstar (he said it himself yesterday) but to us, his fight is not even the most exciting bout on that card. After all, we have Dustin Poirier facing Benoit Saint-Denis in the co-main, Kevin Holland, Gilbert Burns, Petr Yan, and a whole bunch of the most talented rising stars in the promotion.

UFC 299 Co-Main and Main Events

• Bantamweight Title: Sean O’Malley (17-1-0) vs Marlon Vera (21-8-1)
• Lightweight: Dustin Poirier (29-8-0) vs Benoit Saint Denis (13-1-0)

Older fans still remember how Sean lost to Marlon in their original dramatic confrontation, accidentally twisting his ankle. The champ is a rather injury-prone fighter, so such unpleasant moments sometimes happen. However, O'Malley hasn't made any mistakes since then, defeating Petr Yan, Aljamain Sterling, and pretty much clearing the remaining top guys in the division.

One of Vera’s strengths is his strong jaw; he has never lost ahead of schedule, although he has as many as 8 defeats on his record. Marlon prefers to fight standing up, but he has had quite a few submissions in the past. O'Malley, in turn, is a pure striker, a talented puncher who poses a threat to any opponent. He will have an advantage in exchanges and we doubt that the fight will translate to the ground at any point.

It will be interesting to see if their history in the cage repeats itself this time around. Vera is undoubtedly buoyed by the fact that he beat O'Malley once before, and the champ is keen to prove that this result was just a misunderstanding on his path to greatness. If you ask us, we would pick the champion for our UFC 299 predictions.

In the co-main event of the UFC 299 fight card, Dustin Poirier will face Benoit Saint-Denis in a surprising five-round battle. After nearly 40 appearances in MMA and over 13 years in the UFC alone, “The Diamond” has faced every single legendary figure in the modern history of this weight class and fought for the title on several occasions.

Saint-Denis entered the roster as a huge prospect and was humbled by dos Santos. This early defeat led to the decision to move to his natural weight class (lightweight), where he is now on a 5-0 streak.

Our opinion is that matchmakers threw Saint-Denis in the deep waters with this bout and it is too early for him to face a guy like Poirier. Dustin is better in all aspects, he has better boxing, endurance, positioning, and also wrestling skills. We definitely believe that Dustin is the right pick for our UFC 299 predictions.

UFC 299 Main Card

• Bantamweight Title: Sean O’Malley (17-1-0) vs Marlon Vera (21-8-1)
• Lightweight: Dustin Poirier (29-8-0) vs Benoit Saint Denis (13-1-0)
• Welterweight: Kevin Holland (25-10-0) vs Michael Page (21-2-0)
• Welterweight: Gilbert Burns (22-6-0) vs Jack Della Maddalena (16-2-0)
• Bantamweight: Petr Yan (16-5-0) vs Song Yadong (21-7-1)

Michael Page is finally making his UFC debut at 36 after spending the last ten years in Bellator. His opponent is the mediocre Kevin Holland, who is still losing all his serious fights, alternating them with victories over other mediocre fighters. Despite his age, Michael still looks dangerous, recently losing only to the powerful Logan Storley for the Bellator Welterweight World Championship.

It seems that the athletes’ potential is quite comparable, the only thing that confuses us is Holland’s more diverse arsenal and his experience in confronting top opposition. This is a tough one but we believe that Holland is the one to pick for our UFC 299 predictions.

Next up on the UFC 299 fight card, we have an absolute banger – Gilbert Burns vs Jack Della Maddalena. After a close fight with Khamzat Chimaev, “Durinho” was able to score victories over Masvidal and Magny, but lost a decision to Belal Muhammad in his last outing.

27-year-old Jack Della Maddalena has dealt with every opponent he was given in the UFC, including Kevin Holland in his last fight. He is young, fast, and aggressive, and Burns will have a hard time pinning him down. We believe that the safest option here is to bet on a full fight (over 2.5 rounds/fight to reach distance).

Last but not least on the main card, we have the former champion Petr Yan against Song Yadong. Since that controversial first fight against Aljamain Sterling, in which Petr Yan was disqualified after an illegal knee strike, he won only one of his last four bouts.

Song is one of the hottest prospects at 26 years of age and losing here will not be the end of the world for him. As for Petr Yan, he cannot afford to lose for the 4th time in a row or he can kiss his chances to fight for the title again goodbye.

UFC 299 Prelims & Early Prelims

Prelims:

• Heavyweight: Curtis Blaydes (17-4-0) vs Jailton Almeida (20-2-0)
• Women's Flyweight: Katlyn Cerminara (18-5-0) vs Maycee Barber (13-2-0)
• Lightweight: Mateusz Gamrot (23-2-0) vs Rafael Dos Anjos (32-15-0)
• Bantamweight: Pedro Munhoz (20-8-0) vs Kyler Phillips (11-2-0)

Early Prelims:

• Light Heavyweight: Ion Cutelaba (17-9-1) vs Philipe Lins (17-5-0)
• Middleweight: Michel Pereira (28-11-0) vs Michal Oleksiejczuk (19-6-0)
• Heavyweight: Robelis Despaigne (4-0-0) vs Josh Parisian (15-7-0)
• Flyweight: CJ Vergara (12-4-1) vs Assu Almabayev (18-2-0)
• Women's Flyweight: Joanne Wood (16-8-0) vs Maryna Moroz (11-5-0)

The prelims and early prelims of the UFC 299 fight card are as stacked as possible. This line-up would make for one of the best Fight Night main cards on a different week. We picked a couple of matches from the remaining card to analyze in-depth and complete our list of UFC 299 predictions.

Firstly, the featured prelim between Curtis Blaydes and Jailton Almeida. This fight should have already happened a while ago but Blaydes pulled out at the last minute.

Almeida is unlikely to sort things out with Blaydes in a standing position as he is inferior to him in this aspect. Instead, we expect him to try and get an early takedown and try to win by control and ground and pound.

Clearly, this is not expected to be the most exciting fight and we will probably see less fighting than it is expected from heavyweights. We recommend betting on Over 2.5 rounds.

Last but not least, one of our favorite bouts on the UFC 299 fight card is Mateusz Gamrot vs Rafael Dos Anjos. Mateusz is 33 years old, has excellent wrestling with overall good control, a good arsenal of kicks and punches, and is quite active and aggressive. He defeated Fiziev, Ferreira, and Tsarukyan, and only lost to Dariush in a very competitive display. We believe that the Pole is one of the main contenders for the belt in the near future.

Rafael Dos Anjos is a former UFC Lightweight champion but his peak was nearly a decade ago. Nowadays, at 39 years old, he comes out only to complete his contract and win some money. He has good skills on the ground but his defense against takedowns is weak, which could be key for Gamrot. Anjos has also had serious struggles against pronounced strikers like Fiziev, Luque, Covington, etc. In other words, it is easy to pick Gamrot for our UFC 299 predictions here.

Vlad is a former amateur MMA fighter. After a series of injuries, he found a different way to connect with the sport and its fanbase - through writing. He's been covering everything-UFC for over 5 years on various platforms and has been part of the team at NYFights since early 2022.