Wineland was born in Houston, Texas, on June 26, 1984, and has one younger brother. Wineland grew up competing in wrestling and graduated from Chesterton High School in Porter County, Indiana, when he was 17 years old. He began his training for MMA with a friend at Duneland Vale Tudo. Two months later, Wineland fought a 37-year-old man and won. Wineland’s brother is an inspiration for his fighting career. When his brother was two years old, he burned 98% of his body in an accident.

Wineland was defeated by Rani Yahya via first round submission on April 5, 2009 at WEC 40.

Wineland defeated Manny Tapia via unanimous decision on October 10, 2009 at WEC 43.

Wineland was scheduled to face Rafael Rebello on January 10, 2010 at WEC 46, but Rebello was forced off the card with an injury and replaced by George Roop. He won via unanimous decision.

Wineland was scheduled to face Charlie Valencia on June 20, 2010 at WEC 49, but Valencia was forced off the card with an injury. Wineland eventually faced Will Campuzano. Wineland defeated Campuzano via second-round TKO, earning Knockout of the Night honors.

Wineland was expected to face Damacio Page on November 11, 2010 at WEC 52. However, Wineland was forced out of the bout with a shoulder injury and replaced by Demetrious Johnson.

Wineland then faced Ken Stone on December 16, 2010 at WEC 53. He won via KO due to a slam in the first round, earning his second straight Knockout of the Night award.

On October 28, 2010, World Extreme Cagefighting merged with the Ultimate Fighting Championship. As part of the merger, all WEC fighters were transferred to the UFC.

In his UFC debut, Wineland faced former WEC Featherweight Champion Urijah Faber on March 19, 2011 at UFC 128. Wineland lost the back and forth fight via unanimous decision.

Wineland fought Joseph Benavidez on August 14, 2011 at UFC on Versus 5. He was defeated by Benavidez via unanimous decision (30-27, 30-27, 30-27).

Wineland was expected to face Demetrious Johnson on January 28, 2012 at UFC on Fox 2 However, on December 10, Dana White stated Johnson had been pulled from the bout and be a participant in the UFC’s inaugural Flyweight tournament in March. Wineland was then expected to face Johnny Bedford. However, Wineland himself was forced out of the bout with an injury and replaced by promotional newcomer Mitch Gagnon.

Wineland next faced Scott Jorgensen on June 8, 2012 at UFC on FX 3. Wineland defeated Jorgenson via second-round knockout, notable for the fact it marked the first time the durable Jorgensen had been stopped via KO. The performance earned both participants Fight of the Night honors.

Wineland faced Brad Pickett on December 29, 2012 at UFC 155. Wineland defeated Pickett via split decision.

Wineland was expected to face then current Interim UFC Bantamweight Champion Renan Barão on June 15, 2013 at UFC 161. However, on May 21 it was confirmed that Barão had pulled out if the bout, citing a foot injury. With, Barão’s departure, Wineland was removed from the card as well.

The bout with Barão eventually took place on September 21, 2013 at UFC 165. After winning the first round, Wineland lost the fight via TKO in the second round after he was dropped with a spinning kick and follow up flurry, forcing a referee stoppage.

Wineland faced Johnny Eduardo on May 10, 2014 at UFC Fight Night 40. He lost the fight via KO in the first round.

After over a year away from the sport, Wineland returned to face Bryan Caraway on July 25, 2015 at UFC on Fox 16. He lost the fight by unanimous decision.

Wineland next faced Frankie Saenz on July 23, 2016 at UFC on Fox 20. He won the back and forth fight via TKO in the third round and also earned a Performance on the Night bonus.

Wineland faced Takeya Mizugaki on December 17, 2016 at UFC on Fox 22. He won the fight via TKO in the first round.

Wineland next faced John Dodson on April 22, 2017 at UFC Fight Night 108. He lost the fight via unanimous decision.

Wineland faced Alejandro Pérez on July 14, 2018 at UFC Fight Night 133. He lost the fight via unanimous decision.

Wineland faced promotional newcomer Grigory Popov on June 8, 2019 at UFC 238. He won the fight via TKO in the second round.

Wineland was expected to face Marlon Vera on March 28, 2020 at UFC on ESPN: Ngannou vs. Rozenstruik. Due to the COVID-19 pandemic, the event was eventually postponed .