[17] After being a runner–up for half of his career, Askren shined as a junior and a senior, becoming the third athlete to ever earn the Dan Hodge Trophy in multiple occasions, as he received the award in both seasons after compiling a combined 87–0 record.

[21][22] One of the most dominant collegiate wrestlers of all time, Askren's "funky" style relied heavily in unorthodox scrambling techniques and was known for his pinning ability as well as his massive afro.

[23][24] His peculiar and uncommon body shape for a wrestler allowed him to complete moves that his competition could not, thus constantly putting them in awkward positions.

[26] Despite his style relying heavily in folkstyle rules, Askren was able to adapt fairly well to freestyle wrestling after his graduation from college.

[27] After working on adapting his style during 2007, Askren claimed the US National Championship in April and followed up by making the US Olympic Team in June.

[28] At the 2008 Summer Olympics, Askren defeated Hungarian István Veréb via fall in the first round, but fell in the quarterfinals to Cuba's Iván Fundora on points.

Later the same year, Askren defeated 2009 world silver medalist Jake Herbert in a folkstyle rules match at the Midlands Tournament.

In May 2019, Askren lost by technical superiority to five–time World and Olympic champion Jordan Burroughs in the annual Beat the Streets benefit event.

[31] After spending a little over a year in retirement from his MMA career, Askren announced a successful hip surgery in 2020 and revealed that he intends to return to competitive freestyle wrestling soon.

Despite being hit with a brutal upkick and almost getting caught in a triangle choke with one minute left, he was able to take down and control Good in every round.

[43] Following his unanimous decision win over Thompson in a non-title affair at Bellator 40 in Newkirk, Oklahoma, Askren revealed that he was moving to Milwaukee to train under Duke Roufus at Roufusport.

[44] Askren successfully defended his title against season 4 welterweight tournament winner Jay Hieron at Bellator 56[45] following a close split decision.

Askren successfully defended his title against season 5 welterweight tournament winner Douglas Lima at Bellator 64 on April 6, 2012, on Good Friday at the Caesars in Windsor, Canada.

Askren once again used his top control wrestling to shut down his opponents grappling, and opened a cut on Amoussou's forehead with an elbow strike.

[49] He dominated the fight with his wrestling and ground strikes, outstriking his opponent by a wide 248 to 3 margin before winning via TKO in the fourth round.

[52] Askren met Bakhtiyar Abbasov, who had been riding a nine-fight win streak, in the main event of ONE FC: Honor and Glory on May 30.

He can put it in the middle of the cage and give it to me, or I can take it the hard way!”[54] Askren faced Suzuki at ONE Fighting Championship: Reign of Champions on August 29, 2014.

[56] The fight was ruled "no contest" after an accidental eye poke from Askren at 2:19 of round 1 rendered Santos unable to continue.

[70] He was knocked out with a flying knee five seconds into the first round, the fastest knockout in UFC history, ending his undefeated run.

[71] Askren faced ADCC World Champion and MMA veteran Demian Maia on October 26, 2019, at UFC on ESPN+ 20,[72] and lost the fight via technical submission in round three.

[75] Since his retirement, as early as 2021, Askren has repeatedly expressed interest in returning for one more bout in mixed martial arts, should he be able to have a rematch with his former rival Masvidal in the right circumstances, should they be presented in the future.

[76][77][78][79] After a back-and-forth on social media,[80][81] Askren fought Jake Paul in a boxing match on April 17, 2021, losing by TKO in round one.