He graduated from high school in June 2004 and his thriving wrestling career there led him to earn an athletic scholarship to wrestle for Cal State Fullerton Titans while attending college at California State University, Fullerton.
While his freshman year during the 2005–2006 season saw him garnering a 14–16 record that included a 10–8 mark in dual matches, his sophomore season saw him bagging an all-inclusive record of 17–14 that included an 11–4 mark in dual matches, with 5–3 in the Pac-10.
During summer of 2006 he went to Ukraine to hone his wrestling skills.
The University Greco Wrestling Championships held in Akron, Ohio in April 2007 saw him finishing at the sixth position in 132.25 pounds. That year he grabbed fourth position at the Pac-10 championship.
The Pac-10 Championships in 2008 saw him earning the fourth place and moving forward he finished second at the Cliff Keen Invitational.
Following his graduation from California State University, Fullerton, this 3X NCAA qualifier considered delving into MMA. He accepted invitation of Mark "The Filipino Wrecking Machine" Munoz, former UFC Middleweight who coached for three years in Cal State Fullerton, and trained with Team Reign for one and a half year.
Thereafter as advised by Munoz, he trained with Team Alpha Male in Sacramento and accumulated an amateur record of 2-0.
He made his professional debut in MMA on March 26, 2010 and defeated his fellow pro debutee, Czar Sklavos via a dominant unanimous decision. He then went on to clinch three successive wins beating Brandon Drucker, Mike Suarez and Taylor McCorriston respectively.
In pursuit of competing on The Ultimate Fighter: Team Bisping vs. Team Miller, he signed with world’s largest MMA promotion Ultimate Fighting Championship in 2011.
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He fought under the bantamweight bracket and defeated Matt Jaggers in the elimination round via TKO. He became the second bantamweight to be chosen for Team Bisping. He then went on to beat Roland Delorme in the quarter-finals and Dustin Pague in the semi-finals to reach the finale.
He faced John Dodson at The Ultimate Fighter 14 Finale on December 3, 2011, marking his official UFC debut. The final fight of the bantamweight tournament saw Dillashaw losing to Dodson via TKO (punches) thus emerging as runner-up in The Ultimate Fighter 14.
On February 15, 2012, at the UFC on Fuel TV 1 he beat Walel Watson via unanimous decision.
He continued his winning spree defeating Vaughan Lee at UFC on Fuel TV: Munoz vs. Weidman on July 11, 2012; Issei Tamura at UFC 158 on March 16, 2013; and Hugo Viana at UFC on Fox 7 on April 20, 2013.
UFC Fight Night 29 held on October 9, 2013 saw Dillashaw losing to Raphael Assunção by split decision. The performance of both the fighters earned them ‘Fight of the Night’ bonus award.
Dillashaw started the following year with a win against Mike Easton at UFC Fight Night 35 held on January 15, 2014.
In an unexpected turn of events Dillashaw was pitted against Bantamweight champion and top 5 pound for pound Renan Barão at UFC 173 on May 24, 2014.
The bout left everyone startled with Dillashaw not only dominating the fight but also emerging as the new UFC Bantamweight champion by beating Barão via TKO (head kick and punches) in the fifth round. It also earned him ‘Fight of the Night’ and Performance of the Night bonus awards.
A re-match was scheduled with Barão at UFC 177 on August 30, 2014, however Barão’s hospitalisation led Joe Soto to replace him. Dillashaw not only thrived in defending his UFC Bantamweight Championship title by beating Soto but also garnered Performance of the Night bonus award, second in a row.
He then successfully defended his title in a re-match against Barão at UFC on Fox 16 on July 25, 2015. The bout in which he beat Barão by via TKO (punches) earned him his third consecutive ‘Performance of the Night’ bonus award.
He left ‘Team Alpha Male’ in October 2015 and started training with his head coach, Duane Ludwig, a retired pro kickboxer and mixed martial artist.
The UFC Bantamweight Championship title slipped his hands when former champion Dominick Cruz defeated him at UFC Fight Night 81 on January 17, 2016. However the fight earned him Fight of the Night bonus award.
Following the title loss, Dillashaw won a re-match against Raphael Assunção that was held at UFC 200 on July 9, 2016. He rounded off that year with a win against John Lineker at the UFC 207 held on December 30, 2016.
A bout between Dillashaw and present UFC Bantamweight champion Cody Garbrandt was scheduled on July 8, 2017 to serve as headliner for UFC 213. However Garbrandt’s back injury led him to withdraw from the fight which is now expected to happen at UFC 217 event on November 4, 2017.