My thoughts on the upcoming big UFC 299

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The final card of the third century of the UFC’s numbered events promises to deliver in leaps and bounds. The UFC has created an incredible card for fans and I, for one, am very excited for my Saturday night. As the cards have rolled in this year, they have, as expected, been getting better and better. That is mostly due to the strength of the cards increasing, and they are hitting a huge high point this weekend. It’s a curious fight card – the prelims alone could make up a very impressive fight night card. Almeida vs Blaydes, which is essentially a title eliminator for the Interim Heavyweight belt against Tom Aspinall, headlines the prelims. Of the other 6 fighters in the prelims, 5 are ranked. If I had the time, the entire prelim card would be getting a breakdown as well because there is talent left, right, and centre throughout the card.

But, let’s stick to the task at hand. The main card is similarly ridiculous, coming with storylines, prospects and bona fide studs throughout. I feel like the UFC are trying to legitimise the headliner – Sean O’Malley – as a superstar for the company, so as a result they have thrown some amazing fights in below him. Well that is a very welcome decision from me. It’s our last major card before the milestone UFC 300, and these fighters have just missed out on being on that showcase card so I think they’ll be eager to make a statement.

Here are my UFC 299 main card breakdowns and predictions.

Petr Yan (4) vs Song Yadong (7) – Bantamweight Bout

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Petr Yan comes into this fight with a surprising recent slide. Yan was thought to have the credentials of a dominant champion in the Bantamweight division only a couple of years ago. He was interim champ until he lost it to Aljamain Sterling by a split decision in 2022. Since then, he has lost to the current champion and the current #1 contender, Merab Dvalishvili. 3 losses in a row doesn’t look good, but the quality of opponent is obvious if you look. Yan brings a fierce boxing game and has legitimate claims to be the best striker in the division. He also pushes forward to get crafty takedowns and then drop some ground-and-pound game. He needs this one to go his way; otherwise, it’s 5 losses in 6. Eek.

On the other side of the octagon will be the experienced and deceptively young force that is Song Yadong. Song is just 26 and has 29 professional fights already – he debuted in the UFC when he was 19 and at this point seems destined to be a future champion or at the very least a long-term member of the top 5. He is really well rounded with lovely boxing and kickboxing which are emphasised with crisp attacks. He doesn’t spend too much time grappling but certainly can hold his own in those positions. He is great to watch and has a really exciting future.

This is a brilliant opener for the main card, it’ll most likely be a stand-up banger from two elite strikers. Yan needs this result to go his way and I think he’ll do anything to secure that. I imagine that he’ll be just too much for Song, mixing in some takedowns for the scorecard. Song can bounce back from losing here, and definitely will if that happens. But Yan cannot, and I think he knows that and his skills combined with his desperation will result in a victory by unanimous decision (29-28 x3). Just a quick note that I do think the next most likely result would be a Song knockout. While I back Yan’s chin, don’t be surprised if that happens!

Gilbert Burns (4) vs Jack Della Maddalena (9) – Welterweight Bout

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Woooo this one will be a banger. Tbh so will the remainder of these fights, but there’s something about this one that gets me tingling. Gilbert Burns is a veteran and a stud in the welterweight top 5. He was a bit off the pace against Belal Muhammad back in late April (due to nursing an injury), but apart from that he brings it each and every time. Burns is a brutish striker, demonstrating his firm boxing and also impressive defensive movement in that showing against Khamzat back in 2022. Burns is also an elite BJJ practitioner, despite the fact he won’t necessarily push to exercise it, so he has all bases covered.

Then we get Jack Della Maddalena, this down to earth Aussie bloke who is a phenomenal boxer. I watched some tape of Jack yesterday to get a really good feel for his rise through the UFC and it was a very fun endeavour for my evening. Jack is so good at mixing up his attacks, his kicks go low or at the body, and his boxing mixes headshots and body shots seamlessly. Jack also switches stances constantly (apparently inspired by his similar ability when surfing) which provides further issues for any of his opponents. Jack won’t seek to hit the ground too quickly, but once he has his opponent hurt he can drop in a savage submission such as his RNC against Randy Brown in Sydney 13 months ago.

These two are great fighters and also incredibly likeable. A word on the matchmaking here quickly too. Jack is on the rise and although this is certainly a step-up, Burns feels like the perfect opponent and one that will create a brilliant fight. I’m not massively sure where I fall on the prediction for this. On the one hand, Burns is tried and tested – a steady hand when facing prospects. On the other hand, Jack has looked pretty impressive throughout this 16 (!) fight win streak and Gilbert is 37 now. I think Burns is gonna feel it (eh?!) in the final round when Jack’s body shots have started to slow him down enough. The odds have Jack by a relatively small margin and I think I’m going to be a sell-out and agree. I’ll take Jack Della Maddalena by split decision (29-28 x2, 28-29) in a closely contested bout.

Kevin Holland (13) vs Michael “Venom” Page – Welterweight Bout

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So now in the featured bout of the card (quite an arbitrary concept, it’s always the third main), we actually have a debut. Michael “Venom” Page, hereafter referred to as MVP, is brand new to the UFC after building a reputation for himself in the rival promotion Bellator. Now I’ll happily confess that I have not ever watched a Bellator card. The UFC’s main competitors (now basically combined) PFL and Bellator (ignoring ONE here) are quite frankly just inferior products. They don’t have anywhere near as much money – as a result they have inferior fighters and inferior production. So I just can’t be arsed to watch it. I pick up on names and reputations – I’ll watch highlights too. I am aware of the big fighters outside of the UFC, but I can’t profess to have watched them. MVP has been a very well-heralded MMA athlete over the last few years. From what I can gather, he is a weirdo. I do mean that positively btw. Firstly, he’s English, so he has earned my backing. Secondly, he is one of those enigmatic strikers who have unique and eye-catching kicks and punches. MVP bounces around with his hands down and flicks in curious strikes. The only fighter in the UFC who might entertain this slightly arrogant approach is Kevin Holland. If MVP wants to find any success in the UFC beyond Saturday, I’d suggest he has to change up his stance moving forward.

Welcoming MVP to the UFC is a fan favourite – Kevin Holland. Holland should be one of everyone’s favourite fighters; he’s funny in and out of the cage, boasts a really impressive and exciting stand-up game, and would always prefer to lose an exciting fight rather than win a boring fight. That means Holland will not chase a finish when he sees a genuine weakness in an opponent; he’ll try to put them away with a highlight-reel shot instead. Holland is always talking to his opponent which adds a fun dimension. He’s got an impressive chin to match his offensive power.

I think this will be a wonderfully fun fight to watch for its entirety. The most pertinent question seems to be: can MVP replicate his relative dominance in other promotions when he comes to the UFC? Kevin Holland is a great litmus test – he sits just outside of the top 10, only loses to really impressive fighters (Jack Della Maddalena and Wonderboy recently), and will allow his opponent to show off their strengths. I’m not really sure what to take here I’ve got to say. My lack of experience watching MVP doesn’t help, especially when I’ve watched about 5 of Holland’s fights. I’ll lean towards Holland by decision (30-27 x3), but wouldn’t be surprised if he was victorious inside the distance.

Dustin Poirier (3) vs Benoit Saint Denis (12) – Lightweight Bout

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Okay I think it’s fair to call this one the people’s main event – it’s certainly my most anticipated fight of the night. Boi these guys can fight but we also finally get to uncover a mystery here…

First up is Dustin Poirier. Appearing for his 30th (!!) time in the UFC octagon, Poirier is a legend of the sport and, on all accounts, an all-round nice guy too. His charity and media work make him the perfect ambassador for the sport. He is very well-spoken and clearly a caring individual. But people don’t love him just for that. Poirier is guaranteed to be involved in an exciting fight, evidenced by the fact that his last fight came in a BMF title fight against Justin Gaethje. He boasts a stunning and unrelenting boxing game, impressive work in scrambles, and an impetus to just keep moving forward. He’s one of those fighters people have to love for what they have done for the sport and what they bring every single time in the octagon.

He is being faced by French phenom, Benoit Saint-Denis. Benoit is coming off a win against then-14th Lightweight contender, Matt Frevola. Frevola caught a fierce head kick in the 1st round, and that is all she wrote. In the interview after the win, Benoit called for an opponent near the top of the lightweight rankings. Many hardcore fans were excited at this prospect, but also doubtful that the UFC would actually give him such a fight. But wouldn’t you know it, they actually did. Benoit is a former French SAS soldier who trained different martial arts as a kid and teenager. He then entered the military, was presumably successful, and made a seamless transition to MMA. He is one scary dude. The fattest cauliflower ears, a resting frown, and a big beard – personally I’d run. In the cage, some rate him as the best pressure fighter in the whole company – or at least certainly up there with Merab Dvalishvili. Benoit pushes a fierce pace and can batter his opponent anywhere. He mixes nice vicious head and body kicks with some effective, straight boxing. As a prospect he is terrifying for the whole of the lightweight division.

And so, I feel as though this one will see the prospect make a massive step in the right direction. My man MMATheory (on instagram) reckons that Poirier shells up when faced with pressure – something I can’t say I have the experience to have picked up on, but certainly adds to the case of a Benoit victory. I think this is a slightly heart over head pick, but definitely one with valid credentials – so I’m going for Benoit Saint-Denis via submission in the second round (RNC).

“Suga” Sean O’Malley (4) vs Marlon “Chito” Vera (9) – Bantamweight Title Bout

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In the main UFC event, we have the new ruler of the Bantamweight division and a man in whom the UFC are putting a lot of faith – Sean O’Malley. O’Malley is being billed as a current/future superstar for the company (whether rightly or wrongly) and here he will face the one man who has tarnished his record. Back in 2020, an upcoming striking phenomenon faced a man who had significant skin in the game – Marlon “Chito” Vera. Chito defied the odds on the night and defeated O’Malley by TKO after severely damaging his leg. O’Malley could essentially no longer stand, and eventually, Chito hit some savage elbows on him on the ground, and the ref stopped it. This is a disputed result, however it speaks volumes that O’Malley wanted this fight as his first title defence, especially given that Chito is coming off of a loss at the hands of another contender, Cory Sandhagen (albeit then with a win over Munhoz in August). Since their first fight, both men have continued on very different yet similarly upward trajectories.

Chito is a highly effective Muay Thai striker and emphasises his game with some outrageous kicks. He has some impressive highlight-reel kick knockouts, including the famous ending of Dominick Cruz, and is a well-established force in the division. His record matches knockout victories with victories by submission which demonstrates his place as a sensational finisher by any means. My problem with Chito, however, is his baffling tactics in the octagon. He undoubtedly possesses the talent to challenge any other fighter in his weight class, but his unwillingness to get going, despite his corner’s encouragement, can see him get stuck chasing a victory when the scorecards are against him.

And this style will not match up well against a man like Sean O’Malley. O’Malley’s trajectory ever since their last meeting has been incredible. Initially, he seemed to be riding a hype train without much backing. But as his UFC career has progressed, his breathtaking striking style has materialised to be nothing short of brilliant. O’Malley controls not only the distance, the pace, and the octagon itself, but also his own composure and accuracy to a truly elite level. There is a reason he has so many highlight knockouts – he’s just unbelievable at striking. He is the sort of fighter that I am very grateful can exist as a champion. Ultimately, fans want to see high-octane stand-up battles which end with devastating knockouts. Although the scale of devastation might not quite be there for O’Malley, the quality of his final shots is there for everyone to see.

I take O’Malley here, but unfortunately, only by decision (50-45, 49-45 x2). Although he is an incredible striker, big knockouts are less likely at these lower weight classes. On top of that, Chito has a solid chin and has been defeated, but not knocked out, by other big strikers. O’Malley will dominate, and his incredible control of everything in the octagon will ensure it be comprehensive.

Just a reminder, all of these UFC fights are free on TNT Sports. If you are in the UK this is a brilliant opportunity to capitalise on. No PPV payments like in the US, just unreal fights on the same subscription you get Champions League football and a prem kickoff on once a week. Enjoy!

You can check out my previous UFC blog here.

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