Jorge Masvidal (Rob Tatum/Combat Press)

Toe-to-Toe: UFC 244 Preview and Predictions

It is no secret that the UFC has always tried its best to stack up the card every time it has visited Madison Square Garden. The past three years at Madison Square Garden has been pretty phenomenal. Both UFC 205 and UFC 217 featured three title fights, and although last year’s UFC 230 was relatively subpar for MSG standards, the injury woes that hit the card did not exactly help, either.

This year, however, the UFC is returning with a bit of a different plan. Rather than stacking up the card once again with title fights, they decided to stack up the card with multiple fan-favorite fights. The main event of the night will feature the “BMF” belt that will be contested between Jorge Masvidal and Nate Diaz. It is quite rare to see the UFC put on a pay-per-view without a single title fight, the last one being UFC 234, where Israel Adesanya faced off against Anderson Silva after Robert Whittaker was forced to withdraw from the card a couple of days before the event. Last time that the UFC purposely put on a PPV without a title fight? Well, we would have to go all the way back to 2016, when Diaz fought against Conor McGregor, ironically.

The co-main event of the night will feature Darren Till’s middleweight debut against Kelvin Gastelum. Till, since starting his MMA career 17-0-1, has suffered two back-to-back losses against Tyron Woodley and Masvidal. Weight cutting has always been a subject involved for Till’s fights, and with this move up to 185 pounds, Till will be hoping to jump right into the title picture at his new home with a win over an extremely dangerous and motivated Gastelum.


The rest of the card will feature more great fights, including Stephen Thompson vs. Vicente Luque, Corey Anderson vs. Johnny Walker, and Kevin Lee vs. Gregor Gillespie.

The event kicks off with three preliminary-card bouts streaming on ESPN+ at 6:15 p.m. ET. The action then moves to ESPN 2 for the remainder of the prelims at 8 p.m. ET. The five-fight main card airs live on ESPN+ pay-per-view at 10 p.m. ET. Combat Press writers Jaewon Paik and Matt Petela preview the action in this edition of Toe-to-Toe.

Jorge Masvidal and Nate Diaz are ready to clash for the “BMF” title. Who wins and how do they do it?

Petela: Jorge Masvidal picks up a win by late-round TKO. It took me a long time to come to that conclusion but each time I see this fight playing out in my mind, I see Masvidal finishing the fight in the fourth or fifth round. The last four fights that Masvidal has won have all been by knockout, and all of those fights have been at welterweight. He had been on the wrong end of four split decisions in the UFC and since then has put an extra emphasis on finishing fights. It isn’t a coincidence that over that time he has become a legitimate contender at 170 pounds.

Finishing Nate Diaz is far from an easy task. Only two men have ever been able to do it, Hermes Franca and Josh Thomson. Franca submitted Diaz in 2006 and Thomson knocked him out with a head kick and punches back in 2013. Outside of those two instances, he has shown tremendous durability and it has become one of the signatures of the Diaz brothers’ mystique.

Both men have tremendous boxing skills and I think this fight will live up to the hype as long as it lasts. It will be a back-and-forth battle with each man having their moments; Diaz landing high volume combinations and Masvidal landing the more powerful shots with pinpoint accuracy. Diaz will ultimately be unable to withstand the power that Masvidal carries deep into the fight and the Cuban street fighter will walk out with his hand raised and the BMF belt wrapped around his waist.

Paik: It is no secret that Diaz looked as good as ever in his last fight. Against an Anthony Pettis who was coming off a knockout win over Stephen Thompson, Diaz put the three-year layoff in his back pocket and dominated the fight. Physically, he looked better than ever, and mentally, he seemed like the Nate Diaz that left the game back in 2016.

However, history has to be considered when considering the winner for this fight. Diaz has struggled against some of the bigger welterweights in the past, the likes of Dong Hyun Kim and Rory MacDonald. Masvidal, on the other hand, has had his fair share of fights against bigger welterweights, in which he was not only competitive, but dangerous against guys like Demian Maia, Ben Askren and Darren Till. Sure, Masvidal also was a lightweight at one point. However, Masvidal has been consistently competing at welterweight since 2015, and piled up experience competing against bigger men, so it is tough to see that he will have much difficulty with Diaz’s strength or size.

The key for Diaz in this fight would be to utilize a similar game plan he did against Pettis, using dirty boxing up close and keeping the pressure on for five rounds. Diaz will have an advantage in reach by a couple of inches, and if he can use his boxing smartly enough, he could have a successful night. Of course, easier said than done.

Ultimately, it comes down to who has more weapons, which I believe is Masvidal in this case.

Darren Till is set for his middleweight debut, which comes against Kelvin Gastelum. Will Till find renewed success in his new weight class, or is he destined to finish the night with his skid extended to three fights?

Paik: Till has had a rough patch over the past year, coming up short for the title against Woodley, and suffering a devastating knockout against Masvidal. As mentioned in the introduction, weight cutting has always been an issue for Till, and there was always a question surrounding his weight cut come fight week. But now that issue is no longer existent.

Whenever a fighter moves up a weight class, it is tough to tell how their performance will be impacted. We have seen guys have great success since moving up a weight class, such as Whittaker, Masvidal, and Till’s counterpart this weekend, Gastelum. But there have also been quite contrary results, as we recently saw with guys like Luke Rockhold, Chris Weidman and James Vick.

Quite frankly, it is difficult to pick Till in this match-up, simply because of who he is fighting. Gastelum is purely one of the best fighters in the division, and easily one of the toughest. Regardless of what happens, it should be a great striking match-up, but I am going to have to go with Gastelum for this fight.

Petela: Till was a huge welterweight and as soon as he broke onto the scene in the UFC people were calling for him to move up a weight class. It’s difficult to imagine that cutting weight to try and get to 170 pounds wasn’t hampering his performance. I think this will be the best version of Darren Till that UFC fans have seen yet.

That being said, his debut at 185 pounds is a daunting task. Gastelum is one of the best middleweights in the world and stood toe-to-toe with Israel Adesanya in one of the best fights in UFC middleweight history. He has an iron chin, fantastic head movement and lightning-fast hands. He will be the shorter fighter going into his showdown with Till but will likely have the speed advantage on the feet and certainly has the better wrestling pedigree.

Till’s chin was a little suspect in his final fights at welterweight and I expect the move to middleweight will give him added durability. The rejuvenation won’t be enough to overcome what Gastelum brings to the table and I expect Till to suffer his third straight loss and have his name firmly removed from consideration as a title contender in any weight class.

What will Johnny Walker’s fight with Corey Anderson reveal about Walker?

Petela: This will show that Walker has more to offer than just flashy first-round knockouts. Walker earned his spot on the UFC roster through the Contender Series and he actually won a unanimous decision en route to getting his contract. Since then he has fought less than three minutes total in the Octagon over his three wins. Those wins have put Walker firmly on the radar of fellow fighters, as well as fans. Anderson will have a plan in place to avoid becoming part of the Johnny Walker highlight reel.

That being said, a win over Anderson will prove to be the best thing for Walker. Anderson is a grinder and likes to implement a wrestling heavy gameplan to wear down his opponents. What a lot of fans don’t know about Walker is that he is a brown belt in Brazilian Jiu-Jitsu and he will be able to counter the wrestling from Anderson with his own grappling. I expect a late second or third-round knockout for Walker as he answers any questions about whether or not he can be a contender for the light heavyweight belt.

Paik: Not only will it be interesting to see how Walker performs against a legitimate top-10 opponent in Anderson, but it will also be interesting to see if his injury affects him at all here. If you recall, Walker dislocated his shoulder during post-fight celebration at UFC 235. While he laughed it off, it was a big scare for the fans, including Joe Rogan.

But Walker has an extremely legitimate competition in front of him this Saturday night. With yet another devastating victory here, he could easily be next in line for a title shot against Jon Jones. It will also be interesting to see if Anderson can take the fight into deeper waters, and if so, how Walker will deal with it. Anderson historically has had issues against opponents who are versatile and powerful. I do see Walker passing the challenge, although I’m not quite sure on the method.

Who’s the biggest winner at UFC 244?

Paik: The biggest winner has to be Jorge Masvidal. Nate Diaz is already one of the biggest stars in the sport, and should Masvidal be able to win, he is likely going to become one of the biggest names. Should he lose, he will still have plenty of respect from the people, considering how much of a fan favorite Diaz is. In the case of a possible draw, they can do it again. I’m sure Masvidal does not mind.

Petela: Vicente Luque. He is on a six-fight winning streak and has been in two unforgettable fights recently. His split decision win over Mike Perry in Uruguay and last-second TKO over Bryan Barberena were both “Fight of the Night” winners but his fight with Stephen Thompson will be the highest profile fight of his UFC career. He also faces the biggest name in Thompson, who has impressive resumes as both a kickboxer and mixed martial artist. I see Luque getting the win and in doing so vault himself up the rankings and into title contention.

Who’s the biggest loser at UFC 244?

Petela: Kevin Lee. He is 1-3 over his last four fights and after struggling to make the lightweight limit, he got submitted in his lone fight at welterweight. He returns to lightweight against undefeated Gregor Gillespie who is a Division I National Champion wrestler and four-time All-American. Lee will get outwrestled and at that point, his future as a contender will be bleak.

Paik: I agree with Matt here, as Lee is in an extremely difficult situation. He faces a legitimate prospect in an undefeated Gillespie, and a loss here could set him back several fights from where he really wants to be. Admirable on Lee’s part for taking a tough challenge, but maybe not the smartest idea.

Which fight is the sleeper match-up on this card?

Paik: It has to be Brad Tavares vs. Edmen Shahbazyan. Shahbazyan was originally scheduled to face Krzysztof Jotko, but Jotko was withdrawn from the card for unknown reasons. Shahbazyan has shown a lot of promise in his young career, and at just 21 years of age, a win over a veteran like Tavares could catapult his career to the next level.

Petela: Andrei Arlovski vs. Jairzinho Rozenstruik. After a three-fight skid, Arlovski bounced back with a win over fellow veteran Ben Rothwell in July. At 40 years old, this fight will test whether or not the former champion has anything left in the tank. He faces an undefeated “Bigi Boy” who finished both of his UFC opponents via knockout. Rozenstruik will add a third name to his list of knockout victims in Arlovski, announcing himself as a new force in the heavyweight division and marking the end of Arlovski as a legitimate UFC fighter.

Pair this card with…

Petela: This is a premium card and it should be paired with a premium drink. Open up the wallet and spring for a bottle of Johnnie Walker Blue. It’s an added bonus that light heavyweight Johnny Walker is on the card. Sip slowly and enjoy the greatest blended Scotch on earth while you enjoy a great night of fights.

Paik: Honestly, could not agree more with the choice of Johnnie Walker Blue more for this card. How fitting.

Fight Picks

Fight Petela’s Pick Paik’s Pick
Pay-Per-View Main Card (10 p.m. ET)
WW: Jorge Masvidal vs. Nate Diaz Masvidal Masvidal
MW: Kelvin Gastelum vs. Darren Till Gastelum Gastelum
WW: Stephen Thompson vs. Vicente Luque Luque Thompson
HW: Derrick Lewis vs. Blagoy Ivanov Lewis Lewis
LW: Kevin Lee vs. Gregor Gillespie Gillespie Gillespie
ESPN 2 Preliminary Card (8 p.m. ET)
LHW: Corey Anderson vs. Johnny Walker Walker Walker
FW: Shane Burgos vs. Makwan Amirkhani Burgos Amirkhani
MW: Brad Tavares vs. Edmen Shahbazyan Shahbazyan Shahbazyan
HW: Andrei Arlovski vs. Jairzinho Rozenstruik Rozenstruik Rozenstruik
ESPN + Preliminary Card (6:15 p.m. ET)
Women’s FlyW: Katlyn Chookagian vs. Jennifer Maia Chookagian Maia
WW: Lyman Good vs. Chance Rencountre Good Rencountre
FW: Julio Arce vs. Hakeem Dawodu Dawodu Dawodu