As far as true grit fighters go, not many can hold a light to Cowboys career and any time anywhere mindset. For years Cowboy gave us memorable fights and highlights that made an impact on MMA. Cowboys career spanned for over 16 years, this list is a brief overview of some of the highlights from one of the wildest fighters to ever grace the game.
- WEC career: Before he was a fan favorite for the UFC Donald was scrapping his way as an up-and-comer in the now-defunct WEC which housed some of the best fighters in the lighter-weight division. Donald left with a record of 6-3-1.
- UFC debut: 2nd round RNC victory over Paul Kelly (FOTN). Donald was coming in on a 2 fight win streak having avenged his first career loss the former WEC champ. He fought veteran Kelly where he put his BJJ skills on display.
- TKO victory over Charles Oliveira: While not necessarily a big win back in 2011, this victory for Cowboy is the definition of an investment. Charles is now the king of 155 and Cowboy just so happened to hold a win over the Brazilian.
- Decision loss to Nate Diaz: This fight was extremely entertaining (won FOTN), while the fight had its back and forth, Nate ultimately dominated this fight. Not many fighters could rattle Donald mentally, but somehow Nate found his way in.
- 2013-2015: During this time Cowboy went on an unprecedented 8-fight win streak beating fighters like Evan Dunham, Eddie Alvarez, Jim Miller, Myles Jury, and avenging 2 losses to Benson Henderson.
- First title shot, Loss to RDA: In his first and only title shot with the UFC, Donald came up short vs RDA who had won the belt from Pettis and was defending for the first time.
- Move to Welterweight: In 2016, Cowboy moved up a weight class and rifled off 4 straight victories over Alex Oliveira, Patrick Cote, Rick Story, and Matt Brown. All finishes! His fight vs Rick Story delivered a combination for the ages.
- Final 3 fight win streak: In his final victorious run, cowboy took out Mike Perry via armbar, Alex Hernandez via angry Cowboy TKO, and finally Al Iaquinta. All 3 were awarded fight of the night.