UFC Fight Night Prop Picks & Parlay: Eyes On This +550 Prop Play From Guida vs. Madsen

MMA handicapper Dan Tom breaks down his UFC Fight Night prop picks and parlay, as well as his analysis of the main event, Cannoier vs. Gastelum
Dan Tom
Fri, August 20, 4:36 AM EDT

UFC Fight Night Prop Picks & Parlay: Eyes On This +550 Prop Play From Guida vs. Madsen

With the UFC in full swing throughout 2021, we here at OddsChecker will be looking to have you covered when it comes to betting on MMA. As a longtime martial arts analyst and gambler, I'll be providing you with everything from technical analysis to my favorite lines in the form of parlays, props, and more for upcoming fight cards.

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UFC Fight Night: Cannonier vs. Gastelum Main Event

The main event for UFC on ESPN 29 features an interesting middleweight matchup between Jared Cannonier (-160) and Kelvin Gastelum (+125).

Although I initially came into this fight with interest in betting the underdog side, my analysis – along with Gastelum's inconsistency – ended up sending me in the opposite direction, as I suspect that Cannonier's trends of attacking legs will serve him well en route to a decision win.

Don't get me wrong: Gastelum's durability and wrestling chops will keep him live throughout this fight, I'm just not sure how much he'll be able to score in said department given his propensity to ensue in scrambles (not to mention the current crop of Las Vegas judges who are prioritizing damage to the point of ignoring grappling).

For this reason, I'll personally be avoiding this fight at the betting window. Unless you're taking a small shot on the dog or sprinkling on prop angles like "goes to decision" at +104 or the over 3.5 rounds at -137, then I suggest you do the same.

Complete Cannonier vs. Gastelum odds

UFC Fight Night Parlay

UFC Fight Night Parlay Leg 1: William Knight @

UFC Fight Night Parlay Leg 2: Brian Kelleher @ -180

2- Leg Parlay @ +141

As I always say, parlaying is a mad man's game in MMA. That said, I'd be lying if I told you that I didn't dabble in them for fun (keyword fun). For this week's parlay, I decided to go with a chalk pairing that could produce plus money early on in the card.

For the first leg, I went with fan-favorite William Knight, who is affectionately referred to as "Thicc Willie" online. Knight faces Fabio Cherant, who is a young fighter who was catapulted up the food chain after attaining a title on the regional scene.

Although I'm sympathetic to Cherrant's story, I suspect that his tendency to sit back and counter will get him outworked by the more active Knight, who I see landing leg kicks on the feet and out grappling him on the ground. Unless Cherrant can catch Knight in his favored guillotine choke, then I see Knight taking this one on the scorecards.

For the second leg of this parlay, I decided to go with Brian "BOOM" Kelleher.

Kelleher draws Contender Series product, Domingo Pilarte, who is looking to bounce back off of a vicious knockout loss and year-plus layoff. Though the latter isn't something you should condemn Pilarte for (as fighters coming off year-plus layoffs are still clocking in with win rates roughly at 58 percent), I do believe the 6-foot bantamweight may be cutting too much to get to this weight class.

For that reason, I'm fairly confident that the more experienced fighter in Kelleher – who is 4-1 against UFC-level southpaws – can find one of his many paths to victory in this fight. Whether it's his improved body and leg work or his ability to counter in the open with reactive shots, I suspect that Kelleher's recent work with Chan Sung Jung will pay off in the form of a finish.

UFC Fight Night Prop Pick

Mark O. Madsen "by submission" @ +550

In another fight where I initially came in interested in the underdog, I find myself, once again, looking in the direction of the favorite instead.

Mark O. Madsen, who faces noted UFC veteran Clay Guida, will undoubtedly be taking his biggest step up in his MMA career to date. However, despite part of me still feeling that this could be a trap spot, I can't help but follow certain stylistic trends (especially when they're backed up by statistics).

Not only does Guida traditionally struggle against wrestlers and strong grapplers, but his propensity to both desperately shoot, as well as turtle to his base in scrambles, tends to make him susceptible to guillotines and rear-naked-chokes in transition, which could be a perfect fit for Madsen and his front-headlock series. Add in the fact that Guida only wins 38.46 percent of fights where his opponent attempts 2 or more takedowns (stat courtesy of @MonkMMAtics on Twitter), and I suspect that Madsen – who averages 12.9 takedown attempts in 15-minute affairs – finds a submission in the ensuing scrambles.

Regardless of what you're betting, good luck and bet responsibly, my friends!

Click here for complete Guida vs. Madsen odds

And if you'd like more of my analysis, feel free to check out my weekly show, The Protect Ya' Neck Podcast.

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