[6] A professional since 2009, Woodley also competed at Strikeforce and was an NCAA Division I collegiate wrestler for the Missouri Tigers, becoming a two-time All-American and Big 12 Conference champion.

The eleventh of thirteen children, he was raised by his mother after his father left the family early in his life.

In high school, he was a two-sport athlete, competing in American football and amateur wrestling.

After graduating from McCluer High School in 2000, Woodley attended University of Missouri and joined their wrestling program.

It was held by Headhunter Productions at the Holiday Inn Select Executive Center in Columbia, Missouri.

[18][19][20] Woodley's next bout was against Nathan Coy at Strikeforce Challengers: Lindland vs. Casey in Portland, Oregon.

[22] On October 9, 2010, at Strikeforce: San Jose, Woodley defeated André Galvão via knockout midway in the first round.

[25] At Strikeforce: Fedor vs. Henderson, Woodley replaced Evangelista Santos and fought Paul Daley.

[32] Woodley faced Jay Hieron on February 2, 2013, at UFC 156 in his promotional debut, replacing an injured Erick Silva.

[42] Woodley next faced Dong Hyun Kim on August 23, 2014, at UFC Fight Night 48, replacing Héctor Lombard.

[49] Woodley faced welterweight champion Robbie Lawler on July 30, 2016, in the main event at UFC 201.

[56][57] For his third title defense, Woodley faced Demian Maia on July 29, 2017, in the co-main event at UFC 214.

[65] Woodley also received his Brazilian Jiu-Jitsu black belt in the cage from Din Thomas following his victory.

[67] In the fifth defense of his welterweight title, Woodley faced Kamaru Usman on March 2, 2019, in the co-main event at UFC 235.

[68] Woodley was dominated for the entire fight and lost by unanimous decision, ending his nearly three-year reign as welterweight champion.

[87] On May 31, 2021, news surfaced that Woodley had been scheduled to make his professional boxing debut against internet personality Jake Paul on August 29, 2021.

[88][89] Woodley became the first man to take Paul past the second round in his professional career, but ultimately lost by split decision.

[92] Woodley and Luke Rockhold are set to coach a group of fighters in an Hardcore FC Fight Show reality TV series for Hardcore FC promotion which will be filmed in the United Arab Emirates over the next six weeks.

[93] Woodley has pursued acting in his spare time and played roles in both Straight Outta Compton, Kickboxer: Vengeance and Sultan, the latter being an Indian movie directed by Ali Abbas Zafar.

On top of all of these other ventures, Woodley also appears in Season 3 Episode 5 of the Netflix show S.W.A.T._(2017_TV_series) as a member of the Jamaican Possy.

[99] When his hometown of Ferguson, Missouri engaged in civil unrest after the shooting of Michael Brown, Woodley publicly condemned the rioting and lootings that took place.