| UFC Fight Night | 06/18 20:25 | - | Phil Hawes v Winn, Deron | 1-0 | |
| UFC Fight Night | 12/19 22:55 | - | Winn, Deron v Arroyo, Antonio | 1-0 | |
| UFC | 03/08 01:00 | - | Winn, Deron v Gerald Meerschaert | 0-1 | |
| UFC Fight Night | 10/19 01:00 | - | Winn, Deron v Stewart, Darren | 0-1 | |
| UFC Fight Night | 06/22 20:20 | - | Winn, Deron v Bruno Silva | CANC | |
| UFC Fight Night | 06/22 20:00 | - | Winn, Deron v Spicely, Eric | 1-0 |