UFC Fight Night 289: Montel Jackson vs Ricky Simon Preview & Prediction

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Eight years after their first meeting, Montel Jackson looks to avenge his UFC debut defeat as he runs it back with fellow bantamweight Ricky Simon.

Montel Jackson vs Ricky Simon facts

What time are Montel Jackson and Ricky Simon expected to walk out? 27 September 2026 at 12:10 am

Where is UFC Fight Night 289: Rosas Jr. vs Barcelos? Meta Apex, Enterprise, USA

Where can I get tickets for UFC Fight Night 289: Rosas Jr. vs Barcelos? Click here for the latest ticket information for UFC Fight Night 289

What TV channel is UFC Fight Night 289: Rosas Jr. vs Barcelos on? UK – TNT Sports / USA – Paramount

Where can I stream UFC Fight Night 289: Rosas Jr. vs Barcelos? UK – TNT Sports can stream the event online via the TNT Sports website and HBO Max / USA – Paramount+ & UFC Fight Pass

UFC Fight Night 289: Rosas Jr. vs Barcelos main card

Raul Rosas Jr. vs Raoni Barcelos (Bantamweight)

Norma Dumont vs Ailin Perez (Women's Bantamweight)

Luis Hernandez vs Sedriques Dumas (Light Heavyweight)

Mehemmedeli Osmanli vs Ilimbek Akylbek Uulu (Bantamweight)

Melissa Amaya vs Valesca Machado (Women's Strawweight)

UFC Fight Night 289: Rosas Jr. vs Barcelos prelims

Brady Hiestand vs Rinya Nakamura (Bantamweight)

Rodolfo Vieira vs Robert Bryczek (Middleweight)

Rodolfo Bellato vs Christian Edwards (Light Heavyweight)

Josiah Harrell vs Elves Brener vs Josiah Harrell (Lightweight)

Montel Jackson vs Ricky Simon (Bantamweight)

John Castaneda vs Alateng Heili (Bantamweight)

Vanessa Demopoulos vs Yazmin Jauregui (Women's Strawweight)

Montel Jackson: “Quik” looks to snap a run of bad luck on the scorecards

Montel Jackson (15-4) has dropped back-to-back split decisions, first to Deiveson Figueiredo in Rio, then to Raoni Barcelos in April in a fight that came down to the finest of margins. Before that, he’d strung together six straight wins, including first-round KOs of Rani Yahya and Da’Mon Blackshear. At 5’10” with a 75.5 inch reach, Jackson has a huge frame for bantamweight and likes to work on the outside, sniping with a deadly straight down the middle. His amateur wrestling pedigree keeps his fights standing, though his volume can dip for long stretches.

Ricky Simon: Relentless pressure wrestler looking to repeat history

Ricky Simon (22-7-1) is 2-2-1 across his last five, most recently fighting Adrian Yanez to a majority draw in March, a result most fans scored for Yanez. Before that, he dropped a unanimous decision to Raoni Barcelos. Simon is a pressure wrestler with a relentless pace, sitting second on the all-time bantamweight takedown list behind Merab, and he’s at his most dangerous on top. He’s also happy to sit in the pocket and slug it out, with more knockouts than submissions on his record, but that willingness to trade leaves him hittable against sharper strikers.

Montel Jackson vs Ricky Simon prediction

These two first met back in 2018, when Jackson stepped in on short notice for his UFC debut and was ground out by Simon over three rounds. That was a very different Montel Jackson and a very long time ago, both fighters are coming into this one sharper and with more experience than before.

There’s a shared opponent worth noting too. Both men lost to Barcelos, but Jackson pushed him to a split decision in which I believe he won, whereas Simon dropped a clear unanimous one. Barcelos is essentially the better version of Simon, good wrestling with sharper boxing, so if Jackson could run him that close, this should be a step down in difficulty.

The matchup hinges on where it takes place. If Simon gets his grappling going, he should be favoured, as Jackson isn’t always the most urgent and has let the clock tick down in the past, costing himself rounds through a lack of output. If Simon wants a striking battle, Jackson should be the clear favourite. He will circle the outside, avoid long exchanges and punish Simon at range, and with Simon being as hittable as he is, there will be moments where the straight down the middle has him hurt.

Simon is tough though, and a finish feels unlikely. Expect Jackson to use his range and wrestling pedigree to keep this standing.

Prediction: Montel Jackson to win