MMA Best Bets: UFC 259

MMA Best Bets: UFC 259

This article is part of our MMA Best Bets series.

Chris's Picks

15 fights (including three title fights!) means a lot of potential betting spots for UFC 259. I cover four plays I love here, including a decision prop on two big light heavyweights, and one last tire-kick on an oft-injured mainstay of the sport. As always, I have limited my looks to lines below (-200), as I feel that anything more expensive is supposed to come in, and doesn't really require a writeup. All lines are taken from the William Hill online sportsbook and are accurate as of the post date of this article. Without any further ado, let's get to it.

Amanda Lemos (8-1-1) vs. Livinha Souza (14-2-0)                             Weight class: Strawweight

I've said previously that it doesn't make sense to bet a fighter straight up if they generally win in a particular fashion. The same rule can be applied to the way their opponents typically lose: if a fighter has a decently long sample size of not being finished, we can reasonably assume they will see the final bell.

Such is the case with Souza, who has never been stopped in 17 professional fights heading into her bout at UFC 259. It may be the case that Lemos has finished all but one of her eight wins, but that exception came in her last bout against Ashley Yoder, which may indicate that she will not be much of a finisher against stiffer competition.

Lemos remains the clear pick because of her physicality and power advantage, but Souza's jiu-jitsu accolades make me comfortable that she can defend herself on the ground, and the fact that she was able to handle the power of someone like Sarah Frota makes me think she won't be easy to stop with strikes.

The play: Amanda Lemos wins via decision: -110

Amanda Nunes (20-4-0) vs. Megan Anderson (10-4-0)                     Weight class: Bantamweight

Want to know how to place a responsible wager on a (-1100) favorite? Play props! In this case, we will specifically be targeting the lack of ground skills possessed by Anderson and the fact that a substantial height and reach disadvantage will likely compel Nunes to take the fight to the mat.

The most glaring test case we have in this regard is Holly Holm's fight with Anderson. Not only did she complete takedowns by (essentially) just running in a straight line until Anderson lost her balance, but "The Preacher's Daughter" was able to effortlessly advance to positions and attempt submissions. We can also look to Anderson's bout with Felicia Spencer, a fight that was finished by rear-naked choke in the first round. Neither of these results should make anyone comfortable that Anderson can survive on the ground with Nunes, who is a black belt in jiu-jitsu.

Oftentimes, I like to take the KO/TKO insurance in spots like these. I opted not to do so in this instance because of what I see as too stark of a price difference (+100 vs. +150), as well as a feeling that this fight will end fairly quickly once it hits the ground, as Anderson barely survived on the mat against a fighter in Holm who has never had a submission victory in 14 professional wins.

The play: Amanda Nunes via submission: +150

Dominick Cruz (22-3-0) vs. Casey Kenney (16-2-1)                             Weight class: bantamweight

Dear reader, indulge me in a thought experiment: what would the line on this fight have been after the trilogy fight with Urijah Faber in 2016? Of course, the injuries that occurred over that space that robbed Cruz of literal years of fight time have to be considered. I'm just trying to illustrate how the skill difference would be perceived if both of these men were actively competing.

The good news for those that want to play Cruz here is he didn't really look all that different in his fight with Henry Cejudo than he did in that bout with Faber. Sure, an argument can be made that he's a step slower, but the general practice of being agile, awkward and hard to hit was maintained by the former champion throughout the course of the fight. It also strikes me that Kenney may be setting a pace he can't keep in these bouts, as he looked noticeably more tired than Nathaniel Wood in the latter rounds of their bout, and one thing that has never been questioned when it comes to Cruz is his gas tank.

One thing we can be sure of is that if Cruz comes out and works Kenney in the way I think he can, it will be a long time before we see a line anywhere close to this for a similar level of competition. I say we capitalize now, as even if Cruz has lost a step, it should still be enough to handle a fighter like Casey.

The play:  Dominick Cruz: +115

Kennedy Nzechukwu (10-4-0) vs. Carlos Ulberg (3-0-0)                   Weight class: light heavyweight

There are a whole host of things that make this fight odd to me. The first is that – barring a publicity stunt fighter like CM Punk or James Toney – I can't remember when a fighter with as little as three professional bouts made their debut with the organization. Mainly, though, I'm surprised that this fight is slated to finish by knockout.

A quick look at the resumes of these two fighters (to the extent that Ulberg has one) doesn't exactly scream "someone is going to sleep," which makes me think this line relies mostly on the fact that we are in a heavier weight class.  While this isn't entirely unfair, it's worth noting that Nzechukwu has been an extreme pressuring counter-fighter during his time in the Octagon, and Ulberg's Contender Series knockout came after spending most of the fight up to that point being backed against the fence.

Both men have undeniable power, so this play could be made to look fairly silly with one shot, but we have seen staring contests between big newcomers (and relative newcomers) in the past, and it seems we are headed for a low-volume grindfest here.

The play: Fight goes to decision: (+138)

Coles Picks

Askar Askarov (13-0-1) vs. Joseph Benavidez (28-7)
Weight class: Flyweight

Askar Askarov is the real deal and will get to prove it on the prelims of UFC 259.

Currently, Askarov is a -137 favorite, which I think is a very fair price. I personally set him at -175, which implies a 63 percent chance of winning. 

Although Benavidez is the more proven flyweight, I do wonder if he is past his prime. He is coming off back-to-back brutal losses to Deiveson Figueiredo where he lost by KO and submission. In the fight he got submitted, he also was knocked down a couple of times in the fight, so I do worry about his chin.

Askarov, meanwhile, is a much-improved striker, as he nearly knocked out Tim Elliott at UFC 246 and beat Alexandra Pantoja earlier this year by picking him apart. Where the Russian will really have success is in the grappling. Benavidez uses his wrestling to win fights, but I actually believe Askarov is the better wrestler and he'll be able to keep it standing and win a decision or possibly get the finish.

The Play: Askar Askarov (-137)

Tim Elliott (16-11-1) vs. Jordan Espinosa (15-8)
Weight class: Flyweight

I don't understand these odds at all, as I believe the opener of Tim Elliott being a -125 is closer to how I lined it off -150 Elliott.

Although Elliott is only a +100 underdog, it still is even money on a fight I believe he should be favored. Although he is just 1-3 in his last four, his losses are to Brandon Royval, Askar Askarov, and Deiveson Figueiredo. He's also fought for the UFC title and has proven himself at flyweight more than Jordan Espinosa.

Why I like Tim Elliott is because of his pace and grappling. Throughout Espinosa's career, he has struggled against grapplers and was choked out by Alex Perez and Matt Schnell. In this fight, I expect Elliott to use his pace and striking to force a bad shot out of Espinosa and he will grab ahold of his neck and get the submission win.

A bonus nugget on this fight, is when I talked to Tim Elliott, this fight was supposed to happen a couple of years ago. However, this was when Elliott was training in Las Vegas and Espinosa was with James Krause, and Krause, a longtime friend of Elliott, told Espinosa he didn't like the matchup for him and told him not to take it. Now, years later, Elliott is now training under Krause and the fight has been made.

The play: Tim Elliott (+100)

Islam Makhachev (18-1) vs. Drew Dober (23-9)
Weight class: Lightweight

Note William Hill doesn't have props out yet, so this line is by DraftKings sportsbook.

Islam Makhachev is the protege of Khabib Nurmagomedov and to me, this is a setup fight for him to get a big win on a big pay-per-view card. Makhachev is currently a -345 favorite which is too high for me to play straight up, but the Russian by submission is at +350, which has a ton of value.

Throughout Dober's career, he has struggled against grapplers. The last three grapplers he fought in Beneil Dariush, Olivier Aubin-Mercie, and Efrain Escudero all took him down and submitted him. I fully expect Makhachev to get Dober down, and I do think if he finishes the fight it would be by submission and at +350 it is worth a shot.

The Play: Islam Makhachev by SUB (+350)

Sean Brady (13-0) vs. Jake Matthews (17-4) & 
Carlos Ulberg (3-0) vs. Kennedy Nzechukwu (7-1)
Weight Class: Welterweight & Light Heavyweight

Sean Brady and Carlos Ulberg are two of my favorite bets on this card, however, their money line is getting too high. Fortunately, parlaying them gives you +102.

Brady is going to be a problem for the welterweight division, as his wrestling is next-level, and his striking is only getting better. Jake Matthews, meanwhile, has had trouble stuffing takedowns. In the UFC, he has a 70 percent takedown defense. I do think Brady will be able to control this fight with the grappling and possibly even get the finish.

The second leg of the parlay in Carlos Ulberg is the fight right after Brady, so you won't have to wait long to see if it cashes. They are also within the first five fights on the event. 

Ulberg is the main training partner of Israel Adesanya and is a decorated kickboxer who has phenomenal standup. Kennedy Nzechukwu, meanwhile, is primarily a striker who gets hit a lot, as he has a striking defense of just 55 percent. I expect Ulberg to just pick him apart for however long the fight lasts. To get plus-money on this parlay is very good value in my opinion.

The Play: Brady & Ulberg parlay (+102)

AJ's Picks

Aljamain Sterling (19-3-0) vs. Petr Yan (15-1-0)
Weight Class: Bantamweight

The implied odds I made for this fight are -150/60% Aljamain Sterling to win. 

Quick thoughts:

I understand Yan being the favorite. He is the champion, and we very often see the champion favored in title fights. Not only that, but Yan is an excellent fighter overall that is very well rounded. That said, I believe stylistically this is a favorable matchup for the challenger Aljamain Sterling.


They're both excellent grapplers overall with a tremendous ability to scramble, so I don't really see this facet of the fight as all too compelling. That said, I do favor Aljamain here. He is the far more dangerous submission grappler (i.e., excellent ability to take the back of the opposition, BJJ Black Belt under Matt Serra, has a threatening guard, and multiple wins via submission). I also see Aljamain as the stronger fighter in the clinch.


First, Yan is an excellent striker, but there are areas of his striking Aljamain can capitalize on. Aljamain moves much more on the feet, making him a less hittable target of the two. Yan is fairly stationary. As a result, we've seen fighters have moderate success landing on Yan (i.e., Rounds 2 and 3 against Aldo, was getting tagged repeatedly by Rivera, knocked down by Dodson). In contrast, Aljamain is very long for the weight class and has excellent distance management, making him a tough target to land on (i.e., he absorbs 1.94 significant strikes per minute per

While the two are at a distance, Aljamain can win very comfortably. Aljamain fights very well at range while utilizing various tools (i.e., front kick, low kick, body kick, head kick, and straight punches). Additionally, he will also hold a four-inch reach advantage here, so I trust him to land at the kicking range more frequently than Yan. 

They both have shown a willingness to throw low kicks in the past, but Aljamain is more persistent with throwing them, and Yan has shown to be more susceptible to them of the two (i.e., was hurt by Aldo and Rivera). 

Another thing is the pace they each push. The stats don't back this up so much, but the eye does when the two are in open space. Yan has shown the tendency to be passive for stretches in several previous fights, whereas Sterling will constantly throw volume with his varied tools. Lastly, each fought Jimmie Rivera, and the results were very different. Sterling very clearly won the fight (i.e., outstruck Rivera 101 to 24 in significant strikes and was in control the entirety of the fight). In contrast, Yan had a much more difficult time (i.e., was out-struck by Rivera 73 to 56).

All in all, it's generally tough to bet against Petr Yan, who is the current champion of this weight class and a tremendous, well-rounded fighter. However, Sterling is the toughest fight for him right now and likely wins this fight. 

TLDR: I am betting Aljamain Sterling here because I favor his grappling advantage (secondary) and his striking advantage (primarily). 

The Play: 2 units @ +115 AND .5 units @ +120 on Aljamain Sterling to win versus Petr Yan

Yadong Song (16-4-0) vs. Kyler Phillips (8-1-0)
Weight Class: Bantamweight

The implied odds I made for this fight are -122/55% Kyler Phillips to win.

Quick thoughts

When I first saw the matchup, I thought to myself, "Man, this a huge step up in competition for Kyler," but once I started to analyze the matchup, I concluded that Kyler is in a good spot. As I watch Kyler fight, I'm like, "does this guy ever get tired"? He truly has a tremendous motor, as we'll discuss under 'Cardio.' Kyler also is very well rounded and gets noticeably better with each appearance in the octagon. 

Honestly, Kyler is one of the most improved fighters I've come across in research regarding a short time frame. He as looked SIGNIFICANTLY better in the UFC than his regional footage. He trains at the MMA lab with other very talented UFC fighters in the 135-pound weight class.  

Lastly, there is the potential that I add more on betting Phillips straight in the future with regards to this matchup. Right now, there are lower max limits set for this fight than there will be closer to fight time. Should Phillips stay the underdog (i.e., +122/45% or better) once the max limits are raised, I will add more to this bet. 


They're both good technical strikers. Yadong is very dangerous, especially early on (i.e., fast, powerful boxing with countering proficiency and good combinations), and he does possess more power in his hands of the two. However, I favor Phillips to win the aggregate of the striking exchanges. He fights better at kicking range (i.e., has a five-inch arm reach advantage and has more variety with his kicks) while pushing the higher tempo. Phillips can also have success with low kicks (i.e., Vera landed 22 of 26 on Yadong), which can score points on the judges' scorecards and hinder the mobility of Yadong. Also, Phillips's striking defense has shown to be solid (i.e., good head movement and keeps a high defensive guard). Therefore, though a big counter KO from Song can happen, it's not as likely here as say it would be against an opponent with susceptible striking defense. 


Song has good first-layer takedown defense (i.e., good athletic sprawl and gave Stamann's wrestling a lot of early resistance). However, as the fight progresses, he can be taken down once fatigued (i.e., he was taken down by Vera's two trips in round 3 and was controlled on the ground for the vast majority of Round 3 against Stamann). Kyler has shown the ability to take fighters down in open space (i.e., single-leg TD and double leg TD). Also, he's shown to take fighters down against the fence (i.e., body lock and footsweep TD ability), he certainly can get this fight to the ground where he holds the Brazilian Jiu-Jitsu advantage (i.e., BJJ Brown Belt and BJJ World Champion). Kyler has excellent ability to take the back of the opposition in transition, is a great guard passer, submission threat in various areas, very positionally aware, and aggressive while in top position with ground & pound. Yadong was mounted and nearly finished by Stamann in Round 3 (i.e., was controlled for the vast majority of the round). Yadong also had his back taken briefly by Vera in Round 3. If Phillips gets in these same dominant positions, I believe he will maintain top control for stretches of the fight and/or earn the finish. 


There is a wide discrepancy here. Song's cardio is not bad, but we've seen him slow down in the UFC more than once (i.e., he was noticeably tired towards the end of Round 2 against Vera and was gassed in Round 3 & mounted, nearly finished against Stamann). In contrast, Kyler has excellent cardio as he can fight at a very high pace for 15 minutes and will pursue the finish on the ground or the feet. 

All in all, Song is an exceptionally talented fighter overall. Still, the areas of his game where he's looked most susceptible (i.e., cardio and grappling), Kyler can exploit and have more success as the fight progresses with his style. Song Yadong can win this fight by early TKO/KO, but I trust Phillips to win this fight if that outcome does not happen. 

TLDR: I am betting Phillips here at the underdog price. I believe he should be favored here due to his higher tempo, superior cardio, diversity & length as a kickboxer, and superior grappling. 

The Play: 1.25 units @ +165 AND 1.25 units @ +145 Kyler Phillips to win versus Song Yadong

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Christopher Olson
Christopher Olson writes DFS articles and blogs for a variety of sports including MLB, NFL and MMA. Follow him on Twitter @RealChrisOlson
AJ Schullo
AJ has been playing DFS ever since his senior year of college. His passion for DFS helped him understand many things about the game, which prepared him for his future sports betting, which he does now and playing DFS. AJ placed in the top 50 at the DraftKings Sports Betting National Championship in 2019 and qualified for the 2018 MMA Knockout King. It's not just these past experiences that have made AJ's DFS and betting journey so incredible but his willingness to never stop leveling up his game by learning and improving his everyday process through constant experience.
Cole Shelton
Cole Shelton is a full-time sports writer focusing on MMA.
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