Best UFC Fight Night Bets: Valentina Shevchenko vs. Alexa Grasso Picks

This is one of the biggest UFC Fight Night cards in recent memory. The rematch between Shevchenko and Grasso could easily co-main event a numbered pay-per-view card, and here we get it for free on TV. You know what else you get for free? Our expert UFC Fight Night betting picks on the card’s top bouts!

What: UFC Fight Night
Where: T-Mobile Arena in Las Vegas, Nevada
When: September 16, 2023

Valentina Shevchenko vs. Alexa Grasso Betting Pick

Last weekend, we saw one of the biggest upsets in UFC title history as Israel Adesanya went down. However, his finishing betting line pales in comparison to what Shevchenko was earlier this year (-1200) when she lost the flyweight title to Grasso. So we’re not surprised that Shevchenko is once again the favorite to win, per the most-used betting sites for UFC.

Fighter
Valentina Shevchenko	-165	-165	-165
Alexa Grasso	+135	+135	+135

We’ll be honest, betting this fight is giving us fits. On one hand, you’re getting an all-time great in Shevchenko at an incredibly friendly betting line. Seriously, anything under -200 is a steal with the best women’s flyweight fighter we’ve ever seen. In the last fight, she missed a leg kick which turned into a submission. So it’s not like Shevchenko was handily beaten by decision. We won’t say it was a fluke loss either, but the point is: Grasso made her pay for one costly mistake.

On the other hand, we also can’t assume Shevchenko is the same fighter we’ve accustomed to seeing either. She’s 35 years old with a lot of miles in her career. Even before the Grasso loss, Shevchenko had a so-so performance against Taila Santos (it ended in a controversial split decision). The days of her running through the women’s division, as she did in her prime, are likely over.

Certainly, on the feet, we’d think Grasso would have the advantage. That appeared to be the case in the first meeting. Plus, if you look at the significant strikes landed per minute stat, you see Grasso outdoes Shevchenko 4.88 to 3.29. The 30-year-old Grasso is Mexican so you know she can box. This fight is also on Mexican Independence Day weekend so the crowd in Vegas will likely be behind the reigning champion.

It’s tough, but we’re backing Grasso to win a second time. We believe Shevchenko might fight rather timid given how the first fight went — not only the tap out, but being outstriked by a younger opponent. Fighting scared typically isn’t a recipe for winning so Grasso gets the ‘W in our book.

Alexa Grasso to beat Valentina Shevchenko

+135

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Jack Della Maddalena vs. Kevin Holland Betting Pick

Phew, talk about a banger of a fight. Here’s another matchup that should be on a PPV undercard. We’re sticking to betting the Maddalena-Holland moneyline because it’s close. Here’s how the oddsmakers have it pegged:

Fighter
Jack Della Maddalena	+120	+120	+120
Kevin Holland	-150	-150	-150

This a prove-it fight for Maddalena. He’s been one of the UFC’s hottest prospects since joining the Contender Series, now having won all six fights in the promotion. However, Maddalena has beaten up a bunch of chumps compared to Holland. In Holland, you’re getting a fighter who’s fought some of the best middleweights and welterweights.

Both are superb strikers. Admittedly, Maddalena is better thanks to his high volume and incredible jab. Still, Holland can really club with his hands. Not only that, but Holland will have a significant 8-inch reach advantage in this bout. That size will make him dangerous, especially given his accuracy when striking.

We don’t want to play conspiracy theorists or anything, but we’ve seen a lot of up-in-the-air decisions lately go in favor of the “rising star.” Sean O’Malley against Petr Yan immediately comes to mind. In a close matchup, we think Maddalena gets the judges nod. Not just because he has the future, but because his high output will make it look like he was the more active fighter.

Jack Della Maddalena to beat Kevin Holland

+120

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Raul Rosas Jr. vs. Terrance Mitchell Betting Pick

Alright, you pretty much have to skip the moneyline on this one. That’s because Rosas Jr. is a lopsided favorite at -800 to win. Unless you’re banking on an upset (we are not), then it’s best to take the Rosas Jr.-Mitchell over/under instead. Bookies have it pegged dead in the middle at 1.5 rounds:

Outcome
Over 1.5 rounds	+220	+220	+220
Under 1.5 rounds	-275	-275	-275

We lean with the over on this one, despite it being the underdog option. Look, Rosas Jr. is a grappler through and through. His striking needs a lot of work so expect to see Rosas diving at legs almost nonstop. In three career UFC fights, he has eight takedowns so he’s actually effective at it.

While we do expect Rosas Jr. to get a submission win, it won’t be as quick as the odds are letting on. The 18-year-old is fresh off his first career loss, and we don’t expect him to come in here and instantly ragdoll Mitchell who is the bigger and more experienced fighter (Mitchell is 15 years older). It’ll be a war of attrition so take the over instead.

Over 1.5 rounds in Rosas vs. Mitchell fight

+220

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How To Bet On UFC Fight Night?

The whole Fight Night card features 10 fights. Those 10 bouts create massive sports betting type opportunities when you factor in moneylines, over/unders, and props. If you want all those UFC Fight Night bets in one place, then visit one of the bookmakers below. Per our latest sportsbook reviews, these are the top-rated sites industry-wide so you’re in good hands all around.