Mixed martial arts career
Early career
Wineland began his mixed martial arts career competing in regional organizations in his native Midwestern United States. He had compiled a total of 15 professional fights before signing with World Extreme Cagefighting.
World Extreme Cagefighting
Wineland became the inaugural WEC Bantamweight Champion after defeating Antonio Banuelos via first-round TKO at WEC 20. Wineland lost the title in his first defense against Chase Beebe by unanimous decision at WEC 26: Condit vs. Alessio.
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.[6]
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.[7] He won via unanimous decision.
Wineland was scheduled to face Charlie Valencia on June 20, 2010, at WEC 49,[8] but Valencia was forced off the card with an injury.[9] Wineland eventually faced Will Campuzano.[10] Wineland defeated Campuzano via second-round TKO, earning Knockout of the Night honors.[11][12]
Wineland was expected to face Damacio Page on November 11, 2010, at WEC 52.[13] However, Wineland was forced out of the bout with a shoulder injury and replaced by Demetrious Johnson.[14]
Wineland then faced Ken Stone on December 16, 2010, at WEC 53.[15] He won via KO due to a slam in the first round, earning his second straight Knockout of the Night award.[16][17]
Ultimate Fighting Championship
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.[18]
In his UFC debut, Wineland faced former WEC Featherweight Champion Urijah Faber on March 19, 2011, at UFC 128.[19] Wineland lost the back and forth fight via unanimous decision.[20]
Wineland fought Joseph Benavidez on August 14, 2011, at UFC on Versus 5.[21] He was defeated by Benavidez via unanimous decision.[22]
Wineland was expected to face Demetrious Johnson on January 28, 2012, at UFC on Fox 2[23] 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.[24] Wineland was then expected to face Johnny Bedford.[25] However, Wineland himself was forced out of the bout with an injury and replaced by promotional newcomer Mitch Gagnon.[26]
Wineland next faced Scott Jorgensen on June 8, 2012, at UFC on FX 3.[27] Wineland defeated Jorgenson via second-round knockout, notable for the fact it marked the first time the durable Jorgensen had been stopped via KO.[28] The performance earned both participants Fight of the Night honors.[29]
Wineland faced Brad Pickett on December 29, 2012, at UFC 155.[30] Wineland defeated Pickett via split decision.[31]
Wineland was expected to face then current Interim UFC Bantamweight Champion Renan Barão on June 15, 2013, at UFC 161.[32] However, on May 21 it was confirmed that Barão had pulled out if the bout, citing a foot injury.[33] With, Barão's departure, Wineland was removed from the card as well.[34]
The bout with Barão eventually took place on September 21, 2013, at UFC 165.[35] 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.[36]
Wineland faced Yves Jabouin at UFC on Fox 10.[37] Wineland won the fight via TKO in the second round.[38]
Wineland faced Johnny Eduardo on May 10, 2014, at UFC Fight Night 40.[39] He lost the fight via KO in the first round.[40]
After over a year away from the sport, Wineland returned to face Bryan Caraway on July 25, 2015, at UFC on Fox 16.[41] He lost the fight by unanimous decision.[42]
Wineland next faced Frankie Saenz on July 23, 2016, at UFC on Fox 20.[43] He won the back and forth fight via TKO in the third round and also earned a Performance on the Night bonus.[44][45]
Wineland faced Takeya Mizugaki on December 17, 2016, at UFC on Fox 22.[46] He won the fight via TKO in the first round.[47]
Wineland next faced John Dodson on April 22, 2017, at UFC Fight Night 108.[48] He lost the fight via unanimous decision.[49]
Wineland faced Alejandro Pérez on July 14, 2018, at UFC Fight Night 133.[50] He lost the fight via unanimous decision.[51]
Wineland faced promotional newcomer Grigory Popov on June 8, 2019, at UFC 238.[52] He won the fight via TKO in the second round.[53]
Wineland was expected to face Marlon Vera on March 28, 2020, at UFC on ESPN: Ngannou vs. Rozenstruik.[54] Due to the COVID-19 pandemic, the event was eventually postponed .[55]
Wineland faced Sean O'Malley at UFC 250 on June 6.[56] He lost the bout via first round knockout.[57]
Wineland faced John Castañeda on February 20, 2021, at UFC Fight Night 185.[58] He lost the fight via first round technical knockout.[59]
Wineland faced Cody Stamann on June 18, 2022, at UFC on ESPN 37.[60] He lost the fight via TKO in under a minute of the first round.[61]
On June 19, 2022, Wineland announced his retirement in a post on social media which he wrote "I didn’t get an opportunity to leave my gloves in the cage but as Jim Morrison once sang this is the end". Wineland thanked the company, the match makers and the fans of which UFC president Dana White also said how Wineland was a "Another one that always will fight anyone, anywhere, anytime. Good dude. We like him a lot and wish him the best in his retirement."[62]
