UFC 244 Diaz vs Masvidal: Betting Odds, Picks, and Predictions

Jorge Masvidal and Nate DIaz - UFC 244 Logo

You DO NOT want to miss this fight card on Saturday. UFC 244 from Madison Square Garden has rabid hardcore fans foaming at the mouth and casuals canceling their plans.

The main event features a fight for the inaugural BMF Title Belt between Nate Diaz and Jorge Masvidal. This is a fan’s dream matchup if there ever was one. Both men are absolute dogs in there, always looking to finish the fight, and never even think about quitting.

It’s been rumored that the winner of this fight will have to defend it against Conor McGregor should he get past his next potential opponent…ehem, Cowboy Cerrone.

In the Co-Main Event:

Liverpool’s Darren “The Gorilla” Till makes his debut at Middleweight against another former 170-pounder, Orange County’s Kelvin Gastelum. Each fighter is incredibly explosive with power from both sides.

Before those two animals are locked in the cage, Stephen “Wonderboy” Thompson faces off against Brazil’s Vicente Luque in a battle of striking styles.

“Wonderboy” has adapted Karate to MMA just about as well as anyone ever. He has proven himself to be a riddle seldom solved before his lead leg chin checks you into Imaginationland. Luque brings a Dutch style of kickboxing to the table with heavy hooks and low kicks.

Everybody’s favorite post-fight interview Derrick Lewis will fight the surprising Blagoy Ivanov on the main card as well. Ivanov will have an advantage in endurance while “The Black Beast” holds a massive edge in striking power.

Detroit’s Kevin Lee will be making the trip back down to 155 from a short and unsuccessful stint at Welterweight against dangerous takedown artist Gregor Gillespie.

At least 4 out of these five fights are main event material and we could say the same about some of the matchups on the preliminary card.

There are even some outrageous prop bets available. More on those in a minute. The betting odds are at the online betting site BetOnline.AG.

Let’s get to the Picks and predictions for UFC 244 Diaz vs Masvidal.

Early Prelim Quick Picks

Hakeem Dawodu (-126) vs Julian Arce (+106)

  • Both men are strikers
  • Arce is a former Golden Gloves boxer
  • Dawodu is an explosive Muay Thai fighter with powerful kicks
  • Hakeem will have the speed and power advantage in a fight that will most likely take place on the feet
  • If Arce can put Dawodu on the back foot, he can win
  • I’ll take the better athlete with more tools and power

Katlyn Chookagian (-155) vs Jennifer Maia (+135)

  • Katlyn will have a 4-inch reach advantage
  • Maia is a decent boxer and a bully
  • Chookagian has been in there with better competition and has a higher ceiling
  • I’ll take the longer, more experienced fighter who I believe is rapidly improving
The Bets


Edmen Shahbazyan (-156) vs Brad Tavares (+136)

It’s hard to believe that Brad Tavares is only 31-years-old. He has been locked in the Octagon with some of the Middleweight Division’s best throughout his nearly decade-long run in the UFC.

Brad has fought Yoel Romero and Robert Whitaker and in his most recent contest, had a 4-fight win streak snapped by the current Middleweight Champion Israel Adesanya.

The Hawaiian-born Tavares has been training out of Las Vegas at Xtreme Couture for nearly 7 years now. I remember this well because before he made his choice of a gym, he sparred with us at Syndicate MMA and I was lucky enough to get 3 minutes of kickboxing with him. He was hitting fast, not hard, which was cool by me seeing as he walks around at about 200 pounds of solid muscle.

Please Note:

His opponent, who is trained by Ronda Rousey’s former coach, is undefeated 10-0 with 2 of his 3 UFC victories coming by the way of first round finish. He went the distance with Darren Stewart in his Octagon debut and was absolutely relentless landing 8 out of 21 takedowns against the powerful Brittish striker.

Brad will undoubtedly be the largest test of Edmen’s young career but I think he has the overall MMA game to pull it off.

Tavares has very solid takedown defense at 77% but Edmen is averaging over 7 takedowns per 15 minutes even though his percentage is just at 38%.

I have a ton of respect for Tavares but I think Edmen will live up to the hype and grind out a decision win.

The Bet

Jair Rozenstruik (-153) vs Andrei Arlovski (+133)

Okay, Andrei did look good in his last fight. He was the underdog and pulled it out.
I remember picking against him and being so mad at myself…for betting on Ben Rothwell!

That guy may not have the typical steroid body but he peaked pre-USADA drug testing and has been a complete mess ever since.

The speed advantage Arlovski had over him in that fight was extraordinary. Andrei has about a dozen confirmed Octagon concussions, though.

Rothwell wasn’t fast enough to catch his chin but Yair is much younger and able. The man from Suriname should KO the former champ early.

The Bet

Johnny Walker (-150) vs Corey Anderson (+130)

This is striker versus grappler. It’s that simple.

Corey is used to being the longer fighter in there but he will be at a reach disadvantage of 3 inches as Walker has nearly a 7-foot wingspan.

The Brazilian, Walker, has 100% takedown defense and that stat will surely be tested on Saturday opposite Anderson who has the best takedown accuracy in the Light Heavyweight Division.

Corey is stiff on his feet and has never been able to really be like water in the Octagon. Walker has one heck of a highlight real in 4 UFC fights including his Contender Series win. He has only needed 21 total strikes landed in his last 3 fights!

His past 3 opponents were all short for the division and Corey is tall. This may take away the flying knee but then again, maybe not.

Walker can jump out of the gym. He has spent the entirety of this fight camp training with great wrestlers in Moscow so I think he will be able to fend off the underdog’s efforts to make this one a ground war.

The Bet

Main Card

Gregor Gillespie (-156) vs Kevin Lee (+136)

Alright, we made it to the main card.

Both of these fighters are extremely talented wrestlers.

Lee has been tested against much better competition than the favorite Gillespie but Kevin failed in most of those step-up fights.

Kevin will be coming back down from Welterweight where he only had one fight and came up short against Rafael Dos Anjos. Making the commitment to go up then coming back down can’t help the weight cut. That’s a big 15 pounds as it’s nearly 10% of the Lightweight limit of 155.

Kevin will have a massive reach advantage and I’ll give him the edge in the striking department. He’s also relocated his training camp to Montreal, Quebec Canada to work with Georges St Pierre under the famed Firas Zahabi.

The weight cut factor worries me slightly but it’s just a 3-round fight so I think their wrestling will cancel out and Kev keeps it simple and wins with the jab just like his new training partner GSP did so many times before.

The Bet

Blagoy Ivanov (-117) vs Derrick Lewis (-103)

Blagoy is one of those guys who just finds a way to win.

Whether it’s better endurance, volume punching, or well-timed clinching, Ivanov is a winner.
I don’t think he will be able to defeat Lewis, though.

“The Black Beast” is always improving the technical part of his game while maintaining just enough recklessness and KO power to keep even the most aggressive strikers frozen.

See Francis Ngannou fight. Okay, don’t see that fight.
It was not a fight. The two men stared at each other the entire time in what was one of the most disappointing “fights” of all time.

Ivanov is just not big enough to use the clinch to tire the Houston native. Lewis also has a giant reach advantage and honestly at the media staredown, Blagoy looked scared.

I used to share a gym with Blagoy and he’s a super nice guy but Lewis is a terrible matchup for him.

I think Derrick gets the TKO early.

The Bet

Stephen Thompson (-108) vs Vicente Luque (-112)

Both men are lethal strikers but one guy is basic while the other shrouded in mystery.

I have love for Vicente but he is very hittable absorbing 5 strikes per minute in his career inside the Octagon.

Thompson, on the other hand, does not get hit much at all. I would say go big on Thompson here as it takes even the best fighters in the division at least 3 rounds to figure out the Karate stylist.

Luque is very linear in his footwork and should be out-pointed fairly easily but Stephen was knocked out very badly in his last appearance against Anthony Pettis who kicked off the cage and landed surprising superman hook.

Pettis attacked the back leg of Thompson which was a genius move but I think “Wonderboy” will have probably shored that hole in his defense up.

It’s been 6 months since the head-bouncing KO and he doesn’t have a lot of mileage on his chin so Stephen should be recovered from the concussion.

The Bet

Kelvin Gastelum (-250) vs Darren Till (+210)

Darren Till is absolutely massive for 170 and his weight cuts were taking a toll on his performances.

Gastelum had the same issues and his chin and power are much better at 185. I expect the same from Till.
If this were a 5-round fight, I would say definitely go with Kelvin but the value on “The Gorilla” here is undeniable.

Gastelum is not a big guy.

I remember meeting him in LA at Combate Americas and thinking, wow, this guy fights at Middleweight?

He can rip shots over the top to catch taller fighters as well as anyone but I think Darren’s boost from not cutting those 15 pounds is being undervalued by the sportsbooks here. Let’s go with the live dog here.

If you want to find out more about the odds for this fight, click here!

The Bet

Jorge Masvidal (-155) vs Nate Diaz (+135)

After Diaz’s last win versus the aforementioned Anthony Pettis, he called out Jorge and the fight was made soon after.

This one will be for the BMF belt. BMF is short for fighters who always go for the finish and their will is never broken. These are my favorite types of fighters.

While mixed martial arts is always a sport, it isn’t always a fight. Some guys are in there playing to the judges’ scorecards and their goal is control.

Money is on the line, so you can’t start questioning guys’ manhoods but you have to respect the ones who are willing to take any chance necessary to get the W.

As far as the stylistic matchup, both are great boxers. Nate is a higher level submission artist but Jorge has the wrestling edge to keep it standing.

While the intelligence of the Diaz brothers is often underrated, I think Jorge will still be the craftier fighter in there and that should make the difference in there.

Masvidal is a bit expensive at (-155) but I think he will land the more significant shots. Can Diaz get to him late in the fight, though? That is the question.

Nate loves to use volume to tire his opponents and hopefully get a desperation shot out of them into his guillotine-waiting grasp.

Jorge is not that dumb, though.

He is coming from a better camp and is clearly at the peak of his career. I like Masvidal here to get it done inside the distance.

How can you have a BMF fight that goes to a decision?

The Bets

Betting Props

If Donald Trump Is Shown or Announced, Will the Fans Boo?

  • Yes: -230
  • No: +190

Okay, this one’s not even close.

He was booed in Washington DC during the World Series.
Yes, he’s from New York but he will get booed again.

I don’t think fight fans are quite as judgy as your typical sports fans but baseball fans are fairly conservative and they gave it to him earlier this week.


First Fighter to Bleed

  • Jorge Masvidal: +135
  • Nate Diaz: +140
  • Neither Bleeds: +200

Jorge is a much faster starter.

Nate’s face has enough scar tissue to callous a rhino. I think Nate is the first to bleed.
How cool is this prop bet, though?

I’ve never seen odds quite like this before.


Will Diaz Give the Middle Finger?

  • Yes: +300
  • No: -500

Okay, we know Nate doesn’t respect most of his opponents but he does hold Jorge in high regard.

This is for the BMF title, though, in the land of the middle finger, New York City. Even if it’s more to pump up the crowd, I think Nate flips the bird.

I think the (+300) is golden here.


Will Diaz Land a Stockton Slap on Masvidal?

  • Yes: +250
  • No: -400

Again, slaps are for disrespect but I think respect goes out the window for both men once the Octagon door closes.

The buildup for the fight has been lackluster at best because of said respect and I don’t think it will behoove Diaz to change up his style for anyone.

He has said that he respects Conor McGregor and he slapped him. He even slapped Dana White once.
Give me five across the eyes and the plus money.


Place Your Bets Now!

In Conclusion

There you have it, guys!

There are lots and lots of betting opportunities for you this Saturday. This is one of if not the biggest fight card of the year on paper. I truly hope it lives up to its billing. The stage is set, though.

Madison Square Garden…

West Coast versus East Coast gangsters…

They are both technical boxers that have been around forever. I believe Jorge will be first in the striking exchanges and has the gas tank to withstand a late push from Diaz should this fight go into the championship rounds. I don’t believe that will happen, though.

These two didn’t exactly sell the fight in the buildup so they will leave it all in the cage this Saturday and hopefully finish fighting before 22 minutes and 30 seconds.

The rest of the card is outstanding as well. Have fun with the prop bets but I honestly think they hold more value than some of the fight picks.

Tune in, turn up, and bet hard.

Mike Pruitt / Author

Mike has been covering sports professionally since 2017 but on the amateur scene for 25 years since when he was 12. Before the internet changed the world, he would keep detailed statistical box scores of NFL and NBA contests, write recaps, and voluntarily commentate games and fights alone in his room. Mike's military experience, Bachelors Degree, and employment thereafter were always rooted in engineering, science, and teaching. Now he enjoys being able to express himself through writing about football, golf, and car racing among other sports but most of all fighting as his life has been rooted in mixed martial arts including competing and teaching for the past 15 years.

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