It’s International Fight Week and capping off the days-long event is UFC 239, one of the best looking cards of the year. We don’t have to split up our weekend with a doubleheader, either. In years past, The Ultimate Fighter has always wrapped a season and held the finale during IFW, but we get a reprieve of back-to-back cards this time around, and that’s a good thing because with two title fights and a slew of other intriguing bouts, UFC 239 should demand all our attention.

You’ve come here to take a gander at my underdog analysis, not my ravings about what a great show this will be, so let’s get down to brass tacks. The following four fights are the ones I feel have the most potential to end an upset. Time to take a look at the important elements that could lead to the favorites ending up outside the Winner’s Circle.

Claudia Gadelha $8,800 vs. Randa Markos $7,400

This strawweight matchup is an intriguing one between two very good grapplers. Gadelha is a powerhouse, with an excellent grappling game. The problem is, she’s looked defensively porous in her losses, especially in those to Joanna Jedrzejczyk and Nina Ansaroff, both of whom picked her apart. She starts strong, but good cage control and a fast, forward pace is the way to throw her off her game plan.

Randa Markos is a solid striker with a decent amount of power and above average accuracy. She’s a good clinch fighter and has plenty of durability, which makes her difficult to finish. As a matter of fact, she’s only been finished once in her professional career, giving up an armbar to Cortney Casey. This will be a tough battle, but Markos has everything needed to hand Gadelha another loss.

Prediction — Randa Markos via Decision

Luke Rockhold $8,400 vs. Jan Blachowicz $7,800

Luke Rockhold’s move up to light heavyweight likely should have happened a few fights back, but as the saying goes, better late than never. Despite a couple of losses, Rockhold isn’t some washed up fighter at the end of a steeply declining career. He’s still got plenty left in the tank, however, his periods of inactivity and several run-ins with the injury bug have me concerned more with cage rust than a deteriorating skill set. He’s always had exceptional grappling and capable, although not noteworthy striking, but his array of kicks is mighty impressive, and he uses them well. Again, his inactivity is concerning: two fights in 2015, one in 2016, one in 2017 and his last was in February of 2018. Last thing to note here is headspace. Coming off a demoralizing loss like the one Yoel Romero handed him in his last fight could still have a lingering effect on his psyche. Just some food for thought.

Jan Blachowicz, on the other hand, has been twice as active in the same amount of time, racking up 10 fights to Rockhold’s five. He does have five losses, but it should be noted that he’s massively improved, most notably in his standup. After the early 2017 loss to Patrick Cummins, Jan turned a corner, and demonstrated clear evolution from fight to fight, racking up four wins in a row until he met up with Thiago Santos (no shame there). He’s got a very active jab these days, where before he was dependent on standing and banging, and he’s very offensively effective in the clinch. Blachowicz has a good top game, but his ever-improving technical boxing is what I feel will be the difference-maker. This is such a well-matched contest, but I have a feeling that Rockhold is in for a rude welcome to light heavyweight.

Prediction — Jan Blachowicz via Decision

Ben Askren $8,700 vs. Jorge Masvidal $7500

Decorated wrestler Ben Askren will be facing another tough customer in Jorge Masvidal who most recently starched Darren Till’s collar in London this past March. Askren is coming off a controversial win over Robbie Lawler at UFC 235. Askren’s top control is a smothering lead blanket, and his transitions into full mount are outstanding. Let’s face facts, his transitions into any position of control is almost effortless. His striking is…well, it’s just not good. He’s got a pitter-patter style that’s effective only as far as volume goes, but Ben’s significant strikes are extremely few and far between. His fight with Lawler showed his fight mortality, though, and he came dangerously close to being finished.

This is why I feel Masvidal has an excellent chance to beat him. “Gamebred” is an opportunist and has a keen eye for recognizing an opponent’s weakness (see Donald Cerrone or Darren Till fights). He’s had some past issues with forward movement/cage control, resulting in a questionable decision loss or two, but seems to have made strides to shore that up. He’s also a much quicker starter these days, looking to get the ball rolling right out the gate. Jorge has more than capable grappling, is a fantastic scrambler and managed to take jiu-jitsu ace Demian Maia to a split-decision, even though it was a loss. Where he really shines is his striking, and he’s both technical and powerful. He’s marvelous at landing on his opponents while he’s defending/sprawling (see Demian Maia fight, round two) and also has excellent submission defense. This is Askren’s fight to lose, but I think Masvidal has the necessary tools to take the W here.

Prediction — Jorge Masvidal via (T)KO

Jon Jones $9,600 vs. Thiago Santos $6,600

I know what you’re all thinking to yourselves, “Stephie has lost her mind,” but I promise you, I haven’t. Jon Jones is all that and a bag of chips. He’s an excellent striker, uses his reach and length well, is masterful with his kicks, has outstanding fight IQ and positional awareness — I could go on and on. He’s my vote for GOAT and is one of, if not the most complete fighter in MMA, not just the UFC.

So why have I made the super daring choice to give Thiago Santos consideration? It’s simple—power, and Thiago has loads of it. He’s got insane wattage in his hands (they don’t call him Sledgehammer for nothing!) and rib-cracking, liver-dissolving kicks. It just takes one of those to land and we’ve got a shark in chummed waters ready to finish off its prey. This is a risky pick, but if anyone has a chance to stop Jon Jones, it’s Santos.

Prediction — Thiago Santos via (T)KO

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