Woodley fought his first professional fight on February 7, 2009 against Steve Schnider. It was held by Headhunter Productions at the Holiday Inn Select Executive Center in
Columbia, Missouri. Woodley won via submission in the first round. Woodley's second professional bout was against Jeff Carstens on April 30, 2009. He won the bout via submission in the first round.
Strikeforce Woodley made his
Strikeforce debut against Sal Woods in
St. Louis, Missouri. The fight was at the event
Strikeforce: Lawler vs. Shields on June 6, 2009. Woodley won the fight by submission late in round one. After the win,
Strikeforce signed Woodley to a six-fight deal. Woodley made his second appearance for
Strikeforce on the
Strikeforce Challengers: Kennedy vs. Cummings card. He defeated Zach Light via submission in the second round. On the
Strikeforce Challengers: Woodley vs. Bears card, Woodley had his third fight for
Strikeforce, defeating
Rudy Bears via arm-triangle submission. He won via split decision. On October 9, 2010, at
Strikeforce: San Jose, Woodley defeated
André Galvão via knockout midway in the first round. Woodley fought
Tarec Saffiedine on January 7, 2011, in
Nashville, Tennessee at
Strikeforce Challengers: Woodley vs. Saffiedine. Woodley won the fight via unanimous decision. After the win, Woodley was signed to a contract extension with
Strikeforce. At
Strikeforce: Fedor vs. Henderson, Woodley replaced
Evangelista Santos and fought
Paul Daley. Woodley defeated Daley via unanimous decision. Woodley then fought Canadian prospect
Jordan Mein at
Strikeforce: Rockhold vs. Jardine. Woodley won via split decision. Woodley faced
Nate Marquardt on July 14, 2012, at
Strikeforce: Rockhold vs. Kennedy for the vacant
Strikeforce Welterweight Championship. He lost the fight via KO in the fourth round.
Ultimate Fighting Championship Debut Woodley faced
Jay Hieron on February 2, 2013, at
UFC 156 in his promotional debut, replacing an injured
Erick Silva. Woodley won the fight via KO at just 36 seconds of the opening round. Woodley faced
Jake Shields on June 15, 2013, at
UFC 161. Woodley lost the fight via split decision. Woodley next faced off against
Josh Koscheck at
UFC 167 on November 16, 2013. He won the fight via knockout in the first round. The win also earned him his first
Knockout of the Night bonus award. Woodley next faced former
Interim Welterweight Champion Carlos Condit at
UFC 171. Woodley won via TKO after Condit suffered a knee injury in the second round. On April 8, 2014, Woodley's new eight-fight contract with the UFC was announced alongside his match against
Rory MacDonald at
UFC 174. He lost the fight via unanimous decision. Woodley next faced
Dong Hyun Kim on August 23, 2014, at
UFC Fight Night 48, replacing
Héctor Lombard. He won the fight via TKO early in the first round. The win also earned Woodley his first
Performance of the Night bonus award. Woodley faced
Kelvin Gastelum on January 31, 2015, at
UFC 183 in a catchweight bout after Gastelum failed to make the welterweight limit. He won the fight via split decision. Woodley was expected to face
Johny Hendricks on October 3, 2015, at
UFC 192. It was announced on October 2, 2015, that Hendricks was forced out of the fight due to complications with weight cutting.
UFC Welterweight Championship Woodley faced welterweight champion
Robbie Lawler on July 30, 2016, in the main event at
UFC 201. He won the fight via knockout halfway through the first round to claim the
UFC Welterweight Championship. This win earned him the
Performance of the Night award. Woodley made his first title defense against
Stephen Thompson on November 12, 2016, at
UFC 205. The fight ended in a majority draw with two judges scoring the fight 47–47 and the third 48–47 in favor of Woodley. The rematch with Thompson took place on March 4, 2017, in the main event at
UFC 209. It was another closely contested bout with Woodley winning via majority decision. For his third title defense, Woodley faced
Demian Maia on July 29, 2017, in the co-main event at
UFC 214. He won the fight by unanimous decision. Woodley stated after the contest that he had torn his labrum in his right shoulder in the opening round. Woodley would later have reconstructive surgery to repair the damage. Woodley next defended the
UFC Welterweight Championship against
Darren Till on September 8, 2018, at
UFC 228. He won the fight via submission in the second round. This win earned him the
Performance of the Night award. Woodley also received his
Brazilian Jiu-Jitsu black belt in the cage from
Din Thomas following his victory. Woodley also gave Till his first loss in MMA. In the fifth defense of his welterweight title, Woodley faced
Kamaru Usman on March 2, 2019, in the co-main event at
UFC 235. Woodley was dominated for the entire fight and lost by unanimous decision, ending his nearly three-year reign as welterweight champion.
Post-championship and career decline A rematch with
Robbie Lawler was expected to take place on June 29, 2019, at
UFC on ESPN 3. On May 16, 2019, it was reported that Woodley suffered a hand injury and was pulled from the fight. Woodley was scheduled to face
Leon Edwards on March 21, 2020, at
UFC Fight Night: Woodley vs. Edwards. However, the restrictions related to COVID-19 forced Edwards to withdraw as the event was meant to be moved from London to the United States, and the event was subsequently postponed indefinitely. Woodley faced
Gilbert Burns on May 30, 2020, in the main event at
UFC on ESPN: Woodley vs. Burns. Woodley would again be dominated for most of the fight and lose via unanimous decision. Woodley fought at
UFC Fight Night: Covington vs. Woodley against longtime rival
Colby Covington on September 19, 2020. Similar to his past two fights, Woodley was dominated for four rounds, and eventually the bout was called as a technical knockout after he tapped out during the fifth round due to a rib injury. Woodley faced
Vicente Luque on March 27, 2021, at
UFC 260. Uncharacteristically, Woodley came out swinging aggressively early into the bout, and after rocking Luque and being rocked himself multiple times on the feet, he was defeated by D'Arce choke in round one. This fight earned him the
Fight of the Night award. Weeks later, it was announced that Woodley had fought out his contract after eight years competing in the promotion.
Global Fight League On December 11, 2024, it was announced that Woodley was signed by Global Fight League. On January 25, 2025 Woodley was drafted first. However, all GFL events were postponed indefinitely. == Professional boxing career ==