Jon Jones (Dave Mandel/Sherdog)

Toe-to-Toe: UFC 239 Preview and Predictions

Time flies, doesn’t it? It feels like just yesterday when we witnessed Daniel Cormier become the heavyweight champion of the world by knocking out Stipe Miocic at UFC 226. But no, a year has passed since then, and here we are now, once again at the door of International Fight Week and a UFC pay-per-view — UFC 239.

The main event of the card features light heavyweight titleholder Jon Jones aiming to make his second title defense since regaining the championship in December. Jones goes up against the ever-so-dangerous Thiago “Marreta” Santos.

To add to a main event that features a man whom many consider to be the greatest male fighter of all time, the co-headliner features the new consensus greatest female fighter of all time, Amanda Nunes. The Brazilian sets out to defend her bantamweight title against Holly Holm, who is no stranger to fights with seemingly unstoppable champions. Nunes looks to make her fourth title defense and extend her current eight-fight winning streak.


The list of top-class fights does not stop there, as welterweights Ben Askren and Jorge Masvidal clash. It is turning out to be more than just an interesting battle between skilled fighters. Somewhere, somehow, Askren and Masvidal started to dislike each other.

Do you think this card is awesome yet? Just wait, because there’s more.

Luke Rockhold will also make his return on the card, but this time in a move up to light heavyweight. We haven’t seen Rockhold since February 2018. He will be welcomed to his new division by No. 6-ranked light heavyweight Jan Blachowicz.

Michael Chiesa will also make his second appearance at welterweight, where he faces Diego Sanchez. Gilbert Melendez will make a return for the first time in two years to take on one of the United Kingdom’s top prospects, Arnold Allen. Elsewhere on the card, Claudia Gadelha faces off against fellow strawweight Randa Markos.

UFC 239 takes place at the T-Mobile Arena in Las Vegas on Saturday, July 6. The early prelims will begin at 6:15 p.m. on UFC Fight Pass. The remainder of the preliminary card airs live on ESPN at 8 p.m. ET. The main card will be available through pay-per-view, exclusively on ESPN+, beginning at 10 p.m. ET. Combat Press writers Matt Petela and Jaewon Paik preview the action in this edition of Toe-to-Toe.

Will Thiago Santos become the first man to legitimately defeat Jon Jones?

Petela: Maybe one day I will stop believing that Jones is due to have an off night. He has repeatedly shown that he is one of the best to ever put on a pair of four-ounce gloves, if not the very best. However, I have a feeling that Santos is going to pull off a stunner and upset the champ.

Jones has an incredible ability to calculate range and avoid taking clean shots, but 25 minutes is a long time to avoid the power of Santos. “Marreta” has knocked out his last three opponents, all since making the move up a weight class to light heavyweight. His last loss came at the hands of David Branch, who closed the show and knocked out Santos halfway through the first round of their 2018 fight. The caveat is that the fight was contested at 185 pounds, and the weight cut may have resulted in the weakening of Santos’ chin. In the wins over Eryk Anders and Jimi Manuwa, the former Brazilian army paratrooper showed that his jaw isn’t made of glass.

It’s going to be difficult for Jones to finish Santos on the feet. The clear wrestling advantage goes to the champion, but Santos is a black belt in jiu-jitsu and should be able to stifle the bulk of Jones’ offense if the fight goes to the canvas. The best chance for Santos is to surprise Jones with his aggressive offense near the opening of each round. The Brazilian has five chances to do so, and I like those odds.

Santos will join the ranks of Matt Serra, Chris Weidman, Frankie Edgar, T.J. Dillashaw and Holly Holm as underdogs who dethrone seemingly unbeatable reigning champions.

Paik: It’s true that we have yet to see Jones have an off night. Some are still waiting for it, even if it may never happen.

However, the reason for believing that Santos has a good chance at upsetting Jones this weekend is pretty valid. The man we call “The Sledgehammer” has been on a phenomenal run ever since moving up to the light heavyweight division. He has had three fights in the division, finished all of them, and done so in some of the most devastating fashions, too.

But here’s why the likelihood of an upset is extremely slim:

As mentioned, Santos has finished all of his wins since moving up to light heavyweight. He has yet to see championship rounds despite fighting in two main events. If Santos is to get the upset, his biggest chance would come by a knockout early in the fight. What happens when the fight goes into deeper waters? What happens if it drags out into the championship rounds? Will Santos really be able to keep up with Jones, who has done it countless times? I don’t think so.

As good as Jones is, I have never been a massive fan of his due to all the controversies. Yet, credit must be given where credit is due. Let us not forget who we are talking about here. Despite all the controversies, Jones always happens to come out on top.

Holly Holm gets her first crack at breakout star Amanda Nunes in a bantamweight title clash. Does Holm’s style give her a better chance than Cristiane “Cyborg” Justino at victory over the two-division queen?

Paik: Well, this is an excellent question, and a tricky one indeed. Styles make fights. Now, stylistically speaking, Holm is a less aggressive fighter than Cyborg, and she also fights much more around counter striking. We saw the mistake that Cyborg made in her fight against Nunes, which was being far too aggressive, far too early, and she paid for it.

It would be tough to sit here and say that Holm matches up better stylistically against Nunes, though. When it comes down to it, considering how good of a fighter Nunes is, there is no real “great match-up” against her without being a specialist in an area. Even that might not be such a great match-up, however, considering how well rounded Nunes is in her game.

If there is one weakness that we have seen from Nunes in the past, it is her cardio. However, this has not been the case recently. She was able to go five rounds with Valentina Shevchenko and finish Raquel Pennington in the fifth round. Yet, Holm is a volume striker, and her chances will get better the longer this fight goes.

It is difficult to bet against Nunes. The Brazilian has not lost since 2014, after all. Holm most certainly has ways to win in this one, though. She just needs to do all the right things.

Petela: Holm certainly has a better chance of not getting knocked out within the first minute and making it a competitive fight, but she does not have a better chance to win.

The only person to go the distance with Nunes since 2014 is the aforementioned flyweight champ Shevchenko. Nunes has had two close fights with Shevchenko. Their UFC 215 rematch ended in a somewhat controversial split decision, largely due to the counter striking of Shevchenko stifling Nunes’ ability to land with the devastating power she showcased against Ronda Rousey and Cyborg.

Holm, like Shevchenko, does prefer to counter strike. This should keep her safe from falling prey early to “The Lioness” the way pressure fighters have done recently. Nunes was able to outwork and outpoint Shevchenko in the grappling realm, which does not bode well for Holm. In her featherweight debut against Megan Anderson, Holm demonstrated that she is a much improved grappler from the version of herself who lost the belt to Miesha Tate at UFC 196. However, there will still be a large gap between the jiu-jitsu blue belt and Nunes, a jiu-jitsu black belt and judo brown belt.

The cardio issue is a great point, and although Nunes has seemingly rectified the problem, this is her first fight at bantamweight since moving up to featherweight and becoming a two-division champion. How her body reacts to the weight cut could end up being the determining factor if Holm is able to capitalize on any cardiovascular deficits. I don’t foresee Nunes being tremendously depleted, though. Unless she is, the path to victory for Holm will be unpassable.

Julia Avila — do we need to know this name?

Petela: I want to say no due to the talent at bantamweight and her relative inexperience against elite competition. However, if you’ve seen Avila fight, then it’s hard not to think she has a real chance to beat anyone who stands opposite her in the cage.

Avila’s lone defeat is due to a hand injury she suffered less than a minute into her 2018 fight with Marciea Allen. Outside of her pro debut in 2012, she has only been taken the full duration of a fight by former UFC women’s flyweight champion Nicco Montaño.

In her Octagon debut, Avila takes on Pannie Kianzad, who rejoins the promotion on short notice after not receiving a contract as the runner-up on season 28 of The Ultimate Fighter. Avila, who has the incredible nickname “Raging Panda,” will win inside the distance. As tough as a climb will be into the upper echelon at 135 pounds, I wouldn’t put it past her. So, yes, keep an eye on Avila. She could make some real noise.

Paik: Sure, why not? Sooner or later, the women’s bantamweight division will need more contenders to rise to the top of the division to offer the champion some real problems. It is no secret that after this fight, whether Holm or Nunes comes out on top, the line of title contenders is very limited. There’s Ketlen Vieira; Valentina Shevchenko is always an option; and potentially Aspen Ladd could rise up in the near future. Regardless, the division could use some more contenders.

Avila brings an exciting style to the Octagon. She will be worth watching, and she has the real potential to be a threat to many of the bantamweights very soon.

Who’s the biggest winner at UFC 239?

Paik: Well, the fans. If that is too generic of an answer, I’ll dive in a little more and go with the winner of the fight between Jorge Masvidal and Ben Askren.

Askren has a rare opportunity here. Not only could he earn a possible title shot in his third UFC bout, but he’d also jump his arch rival Colby Covington to get a contract with champion Kamaru Usman’s name on it. Timing is everything in this sport, and the way things have been happening, it all seems to be working out for the “Funky” one.

However, Masvidal has an opportunity to steal this opportunity from Askren. Whether Masvidal has a beef with fighters or not, he makes a darn good case for the next title shot with his most recent performance against Darren Till.

Petela: Thiago Santos.

The former middleweight won’t just be the biggest winner of the night, but he may end up being the biggest winner of all 2019 within the UFC. To topple Jon Jones would be an incredible feat, and he will immediately etch himself into MMA history. The light heavyweight division has lacked depth at the top recently, but with the influx of former middleweight champions Luke Rockhold and Chris Weidman, as well as the emergence of prospects-turned-contenders Johnny Walker and Dominic Reyes, there are a lot of fights to keep a close eye on. The division should be a lot more interesting for many fans whose attention has waned with Jones as the seemingly unbeatable champion.

Who’s the biggest loser at UFC 239?

Petela: Holly Holm.

Holm won’t defeat Amanda Nunes, and this will take her record to 2-5 since she landed the head kick heard ’round the world to knock out Ronda Rousey at UFC 193. A loss gives more fuel to the people who write her off as a flash in the pan and further damages her legacy. It should be noted, however, that her loss to Germaine de Randamie was controversial — I scored the bout in her favor — thanks to the two rounds where she was hit cleanly after the bell with nothing more than a stern warning given to de Randamie.

The decision to give Holm this crack at the title has been questioned, and, at age 37, it could likely be her final shot at reclaiming UFC gold. Even if Holm moves up permanently in weight to 145 pounds and the shallow women’s featherweight division, a loss will make the climb back to the top exponentially steeper.

Paik: While Holm is a pretty good pick for this particular conversation, the typical rules don’t seem to really apply to her. She is about to head into her fourth title shot in the UFC, and wins and losses don’t really seem to matter quite as much to her standing with the promotion.

With that being said, the biggest loser on the card is Luke Rockhold, simply due to the chip that is on his shoulder right now. Rockhold, since winning the middleweight title, has gone 1-2 with little activity, and both losses came via brutal knockout. His new division may suit him much better. However, if Rockhold fails to pick up the win on Saturday night, then it will be tough to see him in title contention anytime soon. This may result in even less activity from the former champ.

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

Paik: Well, it may not be all that much of a “sleeper” match up, but the contest between Jan Blachowicz and Luke Rockhold has been (sorta) flying under the radar — understandably so, considering the card that they are on.

Rockhold’s recent losses have not been too kind to his name and legacy. His inactivity has not helped, either. Blachowicz is a tough first fight for Rockhold at light heavyweight. While the fight is only three rounds, the former middleweight champion always has the capability of delivering great fights, and I feel like he’ll add another one on Saturday night.

Petela: It does seem like everything outside of the main and co-main events is flying under the radar, but one that sticks out is Gilbert Melendez and Arnold Allen.

The former Strikeforce lightweight champion Melendez has fought sparsely over the past five years. He has lost four consecutive fights since defeating Diego Sanchez in their “Fight of the Year” bout in 2013. Allen is 14-1 as a professional and has yet to lose in five UFC fights. He has also delivered two “Submission of the Night” performances in wins over Mads Burnell and Alan Omer.

This will not only be a litmus test of what Melendez has left in the tank, but also a fight between two men who rarely, if ever, have fights that aren’t crowd-pleasers.

Pair this card with…

Petela: It’s 4th of July weekend, and this card is loaded with explosive fighters. It only makes sense to grab a box of firecracker popsicles to accompany you. The name speaks for itself, plus the frozen treat will be just what you need to cool down. This card is full of fights that are going to get hot!

Paik: I couldn’t agree more. Right about now, firecracker popsicles sound pretty darn good, and what’s better than the biggest card of the year to match it? Family and firecracker popsicles sounds like the move to me.

Fight Picks

Fight Petela’s Pick Paik’s Pick
Main Card (Pay-per-view, 10 p.m. ET)
LHW Championship: Jon Jones vs. Thiago Santos Santos Jones
Women’s BW Championship: Amanda Nunes vs. Holly Holm Nunes Nunes
WW: Ben Askren vs. Jorge Masvidal Askren Askren
LHW: Luke Rockhold vs. Jan Blachowicz Blachowicz Rockhold
WW: Michael Chiesa vs. Diego Sanchez Chiesa Chiesa
Preliminary Card (ESPN, 8 p.m. ET)
FW: Gilbert Melendez vs. Arnold Allen Allen Allen
Women’s StrawW: Claudia Gadelha vs. Randa Markos Gadelha Gadelha
BW: Alejandro Perez vs. Yadong Song Perez Song
Preliminary Card (UFC Fight Pass, 6:15 p.m. ET)
MW: Jack Marshman vs. Edmen Shahbazyan Shahbazyan Shahbazyan
WW: Ismail Naurdiev vs. Chance Rencountre Naurdiev Naurdiev
Women’s BW: Pannie Kianzad vs. Julia Avila Avila Avila