Ultimate Fighting Championship

Originally travelling to North America, the goal of Taktarov was originally to become an actor but he decided to become a professional fighter in order to gain a visa extension.^[8] In order to get in touch with Hollywood actors, and having watched the Ultimate Fighting Championship event UFC 2, Taktarov contacted the Gracie Jiu-Jitsu Academy in 1994, offering himself to train Royce Gracie in sambo leglocks. Although he was accepted as a training partner after proving his skill against several instructors, he was ultimately rejected due to his inability to pay the fee. Taktarov next contacted the UFC management in order to participate himself for the prize money, being advised that he was already familiar with that kind of competition and had a chance of winning. He was finally accepted into the UFC 5 tournament in April, and would later find out that the Gracie family had previously pressed to keep him out of the UFC.^[6] A week before the event, Taktarov dislocated his knee, but he decided not to pull out of the tournament.^[6]

Taktarov was billed in the event as "The Russian Bear," a stereotypical nickname invented by his manager, and hailed as a Sambo representative, as this was the most exotic martial art in Taktarov's background. However, he stood out for his friendly demeanor, showing an infectious smile to the camera while introducing himself instead of the intimidating faces and postures other fighters were striking.^[7] His first fight was against Kempo Karate expert Ernie Verdicia, whom Oleg quickly submitted by pulling guard, sweeping him between his strikes, and locking an arm triangle choke for the tapout. He advanced round to meet Greco-Roman wrestler Dan Severn, but Taktarov's injured knee limited his performance, already disadvantaged by 55 lbs. Severn took the Russian down, passed his guard and blocked him against the cage wall, where Taktarov was repeatedly hit with knee strikes and headbutts while he tried to look for submissions. As the strikes opened a deep cut on Oleg's face, the referee stopped the fight in Severn's favor.^[9]

After the event, Taktarov went to train with Ken Shamrock in his Lion's Den fighting team. He described this time as: "For a month Ken and I fought together. The guys who later became good fighters, like Frank Shamrock or Guy Mezger, were not any competition for me at the time. The only guy I trained with was Ken, and we had battles behind closed doors. Nobody was allowed to watch them."^[7]

Taktarov returned at UFC 6, whose first round saw him facing Wrestler and Judoka Dave Beneteau. Although Beneteau took Oleg down and stunned him momentarily with punches, Taktarov answered by scoring his own takedown and tapping him out with a guillotine choke in the scramble. His next bout was originally against Patrick Smith, but an injury forced the latter to be replaced by Anthony Macias, who shared promoter and training ground with Taktarov. The Russian submitted him in with another guillotine choke in nine seconds, becoming the fastest submission in UFC history in the process. The fighters were unusually booed by the crowd, who suspected the fight to be a work executed to ease Taktarov's way to the finals.^[10] In any case, Taktarov went to the main event of the night, being pitted against the much larger fighter Tank Abbott in what commentators called a "skill vs. strength" match.^[10] Both Taktarov and Abbott were already tired and dehydrated by the high altitude of Casper, Wyoming, where the event was taking place.^[11]

The bout was hard-fought, with Abbott dominating the grappling exchanges and scoring punches while Taktarov remained patient and counterattacked with a variety of strikes and submission attempts. After 17 minutes of back and forth action, with both fighters looking devoid of energy, Taktarov locked a rear naked choke for the tournament victory. He had to be taken to the hospital right after with an oxygen mask on.^[10] He was later quoted as, "when I went to the hospital after the fight, they said I barely had enough water in my system, only about one gallon."^[11]

Being the reigning tournament champion, Taktarov was set up to fight reigning UFC Champion Ken Shamrock in UFC 7 for the UFC Superfight Championship. Due to his friendship with Shamrock, Taktarov accepted the fight reluctantly and tried to find a way to win without hurting him, although he was unsure whether Shamrock would do the same.^[11] As with the previous fight, Taktarov displayed an important amount of toughness while defending from the bottom, spending most of the match laying defensively on his guard while receiving punishment. The fight had a 30-minute time limit and went into three minutes of overtime, but the result was the same, with Shamrock scoring strikes both standing and through his guard. As there was no judges, the fight finished as a draw.^[12]

Taktarov then entered the UFC's Ultimate Ultimate 1995 tournament. He rematched Dave Beneteau, who according to Taktarov came to the match having greased himself to difficult the Russian's grip.^[11] Unable to throw him, Taktarov resorted to a flying kneebar, and promptly transitioned it into an ankle lock to submit Beneteau. He then went to face Luta Livre exponent and highly regarded UFC 7 champion Marco Ruas. The match was lengthy and slow, with Taktarov trying repeatedly to take Ruas to the ground while the Brazilian caused damage with strikes and made Oleg bleed. After the time went out, however, Taktarov won the decision for his superior aggression during the match. Controversy arose when Ruas's manager Frederico Lapenda complained about the decision.^[11] Despite Taktarov being tired after the bout, he advanced round and lastly met Dan Severn in the finals in a rematch of their fight at UFC 5. The Russian clamped another leglock combination in the first few minutes, which he claimed Severn was going to tap out to before Taktarov was forced to release it out of fatigue.^[11] The Wrestler then scored headbutts and knee strikes from dominant positions until the end of the bout, including an overtime controlled by way of Boxing, which granted him the decision.^[13]

Taktarov ended his UFC career after Ultimate Ultimate, according to him because the management was focused on Shamrock over any other fighter.^[11] However, on 21 November 2003, at UFC 45, the UFC conducted a poll amongst the fans to determine the most popular fighters in the history of the UFC. The fans voted Oleg as one of the top 10 most popular fighters in the history of the UFC.

Post-UFC

After his UFC tenure, Taktarov competed for Japanese promotion Pancrase, where he lost a decision by points to Ryushi Yanagisawa. He then moved to Brazil, where he defeated Joe Charles by submission in World Vale Tudo Championship. There were next talks about a rematch with Marco Ruas, which Taktarov accepted. He even entertained the idea to crash the match with a ringside brawl, which would attract attention by the news media and allow them both to host an anticipated rubber match back in UFC.^[11] Ruas's management seemed to get into the idea of setting up a third fight, with his manager Lapenda even making Taktarov promise to fight entirely standing, but Ruas himself fought to win. With one minute left in the clock, Taktarov finally took Ruas down, but he allowed the bout to end in a draw. However, interest was little and the rubber match never happened.^[11]

Taktarov returned from Brazil with a broken hand, only to find out his manager had put him on a fight against Renzo Gracie for Martial Arts Reality Superfighting in ten days notice.^[11] Come the match, Taktarov took Gracie down, but the anticipated grappling battle never took off. Taktarov's injured hand impeded him from grabbing an opportune leglock on Gracie, who capitalized on the lapse to fire an upkick that knocked down Taktarov. He tried to continue fighting, but the kick had opened a deep cut and the fight was stopped.^[11]

In 1997, Taktarov traveled back to Brazil to fight decorated ADCC grappler Sean Alvarez in the Pentagon Combat event. Despite Alvarez's size advantage, Taktarov knocked him out with newly polished striking skills.^[11] However, he got sent to another match in short notice, this time to Japan in the first ever Pride 1 show on 11 October 1997, facing Canadian heavyweight and UFC veteran Gary Goodridge. Taktarov suffered a frightening knockout loss, receiving strikes even after having been rendered unconscious, and had to be carried out of the arena in a stretcher.^[11] In one of his recent interviews he attributed Goodridge's victory to the peak of the anabolic steroid cycle that Goodridge allegedly went through prior to the fight. Taktarov further asserted that Goodridge's following performances (i.e. a string of losses) clearly indicated the downtrend of the steroid cycle.

On June 10, 2007, Taktarov faced Dolph Lundgren in a celebrity boxing match. He won the decision after five rounds.^[14]

Return to mixed martial arts

Prior to making a successful comeback to the sport in 2007, Taktarov's last bout was in 2001. Taktarov announced in an online radio interview in November 2007 his plans to return to MMA with BodogFight.^[15] He won his debut match against John Marsh at 33 seconds into the 2nd round of the match by submission (kneebar). His last fight was against UFC 14 and UFC 15 heavyweight champion Mark Kerr, again winning by kneebar.

Taktarov retired from mixed martial arts with a record of 17 wins, 5 losses, and 2 draws.