Born in Irving, Texas, Cummings moved to Springfield, Missouri at the age of three. After beginning wrestling in the sixth grade, he attended Glendale High School where he competed in wrestling, as well as football, baseball, and basketball. A state qualifier, he later attended Meramec Community College where he was a two-time NJCAA national qualifier his freshman and sophomore seasons. Due to an injury, Cummings transferred to Missouri State University to finish his degree, majoring in exercise and movement science. It was around this time that he began to training in mixed martial arts, and was 6-0 as an amateur before turning professional.
Cummings made his professional MMA debut in November 2007. He was undefeated for the first year and a half of his career, going 10–0 during that time period with a majority of his wins by TKO or submission. This impressive streak earned him a shot in Strikeforce. He faced Tim Kennedy in the main event of Strikeforce Challengers 3, but lost via submission in the second round. Post-Strikeforce, Cummings fought for various independent organizations and had one appearance for Bellator Fighting Championships. He added 5 more wins and 2 losses to his record during this time.
In January 2013, it was revealed that Cummings was a cast member of. He won his preliminary bout over Nik Fekete quickly by TKO with the first punch he threw. Cummings was selected by Sonnen as his third pick. Cummings faced Dylan Andrews in the elimination round. He lost via majority decision.
Ultimate Fighting Championship
Cummings made his debut against Ben Alloway on August 28, 2013 at. He won the fight via submission in the first round. The win also earned him his first Submission of the Night bonus award. Cummings was expected to face Sérgio Moraes on November 30, 2013 at. However, Cummings and Moraes had to pull out of the event due to injury and were replaced by Sean Spencer and Drew Dober respectively. Cummings was expected to face promotional newcomer Alberto Mina on March 1, 2014 at. However, at the weigh-ins for the event, Cummings came in eight pounds over the welterweight limit. On the advice of his coaches, Mina would not agree to compete at a catch weight, so the bout was scratched from the event. Cummings faced Yan Cabral on May 10, 2014 at UFC Fight Night 40. He won the fight via unanimous decision. Cummings was briefly linked to a bout with Kenny Robertson on July 16, 2014 at UFC Fight Night 45. However, Cummings was pulled from that fight in favor of a matchup with Gunnar Nelson on July 19, 2014 at UFC Fight Night 46 after his opponent Ryan LaFlare was removed from the card. He lost the fight via rear-naked choke. Cummings was expected to face Antônio Braga Neto on July 25, 2015 at UFC on Fox 16. However, Braga Neto pulled out of the fight in early July and was replaced by promotional newcomer Dominique Steele. Cummings won the fight by TKO in the first round. Cummings faced Nicolas Dalby on April 10, 2016 at UFC Fight Night 86, filling in for Bartosz Fabiński. He won the fight via unanimous decision. Cummings next faced Santiago Ponzinibbio on August 6, 2016 at UFC Fight Night 92. He lost the fight via unanimous decision. Cummings faced Alexander Yakovlev at UFC Fight Night 99 on November 19, 2016. He won the bout by submission in the second round. Cummings faced Nathan Coy on April 15, 2017 at UFC on Fox 24. He won the fight via technical submission due to a guillotine choke in the first round. Cummings was scheduled to face Thiago Alves on January 14, 2018 at. On January 13, 2018, it was announced that Cummings injured his skull after a bathroom slip and the bout against Alves was cancelled as no replacement would be sought. Cummings faced Michel Prazeres on May 19, 2018 at UFC Fight Night 129. He lost the back-and-forth fight via split decision. Cummings faced Trevor Smith on December 15, 2018 at UFC on Fox 31. He won the fight by unanimous decision. Cummings faced Trevin Giles on May 18, 2019 at UFC Fight Night 152. He won the fight via a guillotine choke submission in the third round. Cummings faced Omari Akhmedov on September 7, 2019 at UFC 242. He lost the fight by unanimous decision. Cummings was scheduled to face Andrew Sanchez on April 25, 2020. However, on April 9, Dana White, the president of UFC announced that this event was postponed to a future date Cummings is expected to face Alessio Di Chirico on August 29, 2020 at UFC Fight Night 176.
