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UFC 244 Odds, Best Bets and Preview at New York City’s Madison Square Garden

UFC 244 Odds, Best Bets and Preview at New York City's Madison Square Garden


There’s three possibilities as to why you are reading this column: 1) this is your first time; 2) you like getting losing gambling advice; 3) you’re my mom (HI MOM!!).

UFC Singapore was another lost weekend for me, as my picks when 0-2. The slump is real. Three straight losses. But we’ll beat this thing, together. And it starts this weekend at UFC 244.

UFC 244 marks the UFC’s annual November return to the “World’s Most Famous Arena”, Madison Square Garden in New York City. The fight promotion always stacks this card, with as many as three title fights on the bill some years. This year’s card is no exception, as it’s stacked from top to bottom. However, as you scan the fight lineup you’ll notice no title fight. And the main event is between two journeyman fighters with double-digits in both of their loss columns.

But these aren’t your run-of-the-mill journeymen fighters – these are Nate Diaz and Jorge Masvidal, two fan favorites. And they actually are fighting for a title, technically speaking. The “BMF” belt is on the line (stands for the Baddest…. well, you can figure out the rest). And everyone’s favorite action star, Dwayne “The Rock” Johnson, will be presenting this made up belt to the winner on Saturday. Additionally, your president (not mine, I’m Canadian, eh) Donald Trump is tentatively scheduled to show up. Bigly.

The Miami gangster, Masvidal, is the current betting favorite (-165) over Stockton’s finest. But I’m not recommending betting on that fight – probably too close to call. Here’s the two fights that are worth a look, though.

Odds via MyBookie

Derrick Lewis (+105) vs Blagoy Ivanov

UFC 244 Odds, Best Bets and Preview at New York City's Madison Square Garden

Going with a slight underdog with “The Black Beast” Derrick Lewis in my first play. There’s no questioning his opponent, Blagoy Ivanov’s, toughness – that nasty looking scar in the middle of his chest is from the time he got stabbed in the lung in a bar fight. However, Lewis will have a huge size advantage (four inches of height, six inches of reach, and probably at least 10 pounds), athleticism advantage, and massive power advantage (18 of his 21 wins come via KO).

While there’s a good chance he’ll look like he’s sure to lose at any moment during the opening minutes of the fight, and appear to be seriously gassed out, that’s when he tends to be his most dangerous. Look for him to KO Ivanov on the feet, or maul him with ground and pound, as the Bulgarian gets hit more than he dishes out on average.

Jennifer Maia (+130) vs Katlyn Chookagian

UFC 244 Odds, Best Bets and Preview at New York City's Madison Square Garden

I’m recommending another live dog here, and going with Jennifer Maia over Katlyn Chookagian. There’s good reason “Blonde Fighter” is the favorite here – she’s 12-2, with her two losses coming via split decision. She’ll also have the size advantage (in terms of height and reach) in this matchup.

However, she gets hit often (more than she hits her opponent) and Maia is a talented striker who hits hard. She also missed weight her last fight (coming in at 129 pounds instead of 125) so good chance she’ll be the heavier fighter (which means more power) in this one. Worth a play for plus money.

Overall Results for This Column

Record: 24-21
Earnings (based on $100 bet per): (-$295.83)
Return on Investment: N/A

Jeff Fox is the evil genius behind His work has also appeared in SLAM, Athlon Sports, FIGHT! & Fighters Only magazines,, the St. Louis Post-Dispatch, and many other fine establishments across the globe.


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