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The Ultimate Fighting Championship’s 10th-ranked heavyweight will attempt to rebound from an Aug. 8 technical knockout loss to Derrick Lewis when he meets Chris Daukaus in a featured attraction at UFC Fight Night 185 this Saturday at the UFC Apex in Las Vegas. Oleynik, 43, has delivered 46 of his 59 professional victories by submission, including 14 with his patented Ezekiel choke. He has suffered back-to-back defeats just twice in a remarkably consistent career that now spans 74 fights.
As Oleynik makes final preparations for his confrontation with Daukaus, a look at a few of the rivalries upon which he has built his reputation:
Jeff Monson
Oleynik lost a split decision to Monson under the M-1 Global banner in 2012 and had revenge on his mind when the two esteemed grapplers met for a second time a little more than a year later. The rematch was booked as the Oplot Challenge 67 main event on June 20, 2013 in Kharkov, Ukraine. Oleynik utilized an effective sprawl to remain upright during their initial exchanges and proceeded to bludgeon “The Snowman” with right uppercuts and sweeping hooks from both hands. Late in the first round, Monson whiffed on a takedown, retreated to his back and welcomed his counterpart into his guard. Oleynik unleashed his ground-and-pound and drew blood from the American’s nose and mouth while closing in on a potential finish. Only the bell saved Monson, but Round 2 brought more misery. Oleynik punished the two-time Abu Dhabi Combat Club Submission Wrestling World Championships gold medalist with his jab, lured him into a firefight and eventually drove him to the canvas with a clubbing right hand. Monson offered little resistance, as “The Boa Constrictor” assumed top position, progressed to his back and cinched the fight-ending rear-naked choke 3:28 into the second round. It was his first submission defeat in more than 14 years.
Alistair Overeem
Overeem made the best of a difficult situation, as he survived some tense moments against Oleynik—a short-notice substitution for Alexander Volkov—before chopping down the Russian submission savant with knees and punches in the first round of their UFC Fight Night 149 headliner on April 20, 2019. “The Demolition Man” drew the curtain 4:45 into Round 1 in front of a hushed crowd of 7,236 at the Yubileyny Sports Palace in St. Petersburg, Russia. A looping right hand from Oleynik appeared to wobble the former Dream, Strikeforce and K-1 World Grand Prix champion, as “The Boa Constrictor” moved in and engaged the Dutchman at close range. Overeem recovered and eventually turned the tide with a series of knee strikes, becoming the first man in nearly eight years to stop the American Top Team representative. The setback snapped Oleynik’s two-fight winning streak and likely curtailed any possibility of a run at the UFC heavyweight championship.
Fabricio Werdum
Werdum’s welcome was far from warm when he returned from a two-year, United States Anti-Doping Agency-mandated layoff, as Oleynik eked out a split decision over the former heavyweight champion in a featured UFC 249 prelim on May 9, 2020 at VyStar Veterans Memorial Arena in Jacksonville, Florida. All three judges scored it 29-28: Derek Cleary for Werdum, Barry Luxenberg and Chris Lee for Oleynik. In his first appearance in 784 days, Werdum looked tentative and out of sorts. Oleynik swarmed him from the start, swamping the longtime Brazilian jiu-jitsu black belt with power punches. Werdum answered with takedowns in the second and third rounds but failed to capitalize on his moments of opportunity, allowing “The Boa Constrictor” to escape to his feet and away from danger. Oleynik outlanded the two-time ADCC Submission Wrestling World Championships gold medalist by double-digit margins in all three rounds, posting one of the more satisfying victories of his career.