Will Ricky Simon Walk Into Jackson’s Best Weapon?
Avatar photo Jim Mahoney
24.09.2026

Will Ricky Simon Walk Into Jackson’s Best Weapon?

Montel Jackson has spent eight years getting farther away from Ricky Simon. Now the UFC has put Simon directly in front of him again.

Their first meeting came in Jackson’s UFC debut. Saturday’s version is different enough to make the rematch useful rather than nostalgic: Jackson is now the longer, more dangerous finisher, while Simon still brings the wrestling volume capable of turning those advantages into an exhausting argument.

Bookmaker Sportsbook‘s opening line makes Ricky Simon +176 and Montel Jackson -210, with Over 2.5 rounds -195 and Under 2.5 +166.

Ricky Simon Still Knows Where the Door Is

Simon averages 4.49 takedowns per 15 minutes and owns 77% takedown defense. That creates an awkward assignment for Jackson because Simon does not require one clean entry. Repeated wrestling attempts can compress the space where Jackson’s 75.5-inch reach is most useful.

But Jackson is no longer simply the prospect Simon encountered in 2018. He has eight professional knockout victories, seven first-round finishes and considerably more UFC experience behind his defensive reactions.

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Ricky Simon resets after a wrestling exchange during a previous professional bantamweight fight.

Jackson’s Favorite Distance Has Six Inches

The physical geometry is severe. Jackson stands 5-foot-10 with a 75.5-inch reach. Simon is 5-foot-6 with a 69-inch reach. Simon therefore crosses six and a half inches of reach before his wrestling becomes physically available.

Jackson’s problem is what happens after Simon crosses it. His two most recent fights both reached the judges’ scorecards: defeats against Deiveson Figueiredo and Raoni Barcelos. Simon’s March fight with Adrian Yanez also completed all three rounds, ending in a majority draw.

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The Rematch Has Become a Clock

The moneyline asks whether Jackson’s length and finishing threat finally overturn Simon’s wrestling pressure. The total asks less.

Simon has enough wrestling to interrupt Jackson’s preferred range. Jackson has enough takedown resistance and physical length to make Simon repeatedly rebuild his entries. Neither man’s recent evidence demands an early ending.

Eight years later, the fascinating part may be how long it takes either man to prove anything has changed.

Prediction: Montel Jackson by decision.

Betting Lean: Over 2.5 rounds -195.

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Data Snapshot

CategoryRicky SimonMontel Jackson
Record22-7-115-4
Height5’6″5’10”
Reach69″75.5″
Career KO wins78
Career submission wins41
First-round finishes77
Takedowns per 15 min.4.49—
Simon takedown defense77%—
Last fightMajority drawDecision loss

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