Stadium: Stadium Round: 25 Ground: Hardcourt outdoor
| French Open | 2019/05/20 08:00 | Peter Polansky v Darian King | 6-4,6-4 |
| Challenger Puerto Vallarta | 2019/05/04 00:00 | Darian King v Alejandro Tabilo | 1-6,7-5,5-7 |
| Challenger Puerto Vallarta | 2019/05/03 02:45 | Joao Menezes v Darian King | 5-7,5-7 |
| Challenger Puerto Vallarta | 2019/05/01 17:00 | Andres Artunedo Martinavarr v Darian King | 4-6,4-6 |
| Challenger Leon | 2019/04/25 17:00 | James Ward v Darian King | 6-1,6-4 |
| Challenger Leon | 2019/04/23 17:55 | Skander Mansouri v Darian King | 3-6,2-6 |
| ATP Houston | 2019/04/08 18:00 | Darian King v Pedja Krstin | 6-7,5-7 |
| ATP Houston | 2019/04/06 19:55 | Peter Polansky v Darian King | 4-6,1-6 |
| Challenger Little Rock | 2019/06/03 19:55 | Oliver Crawford v Illya Marchenko | 7-5,7-6 |
| Challenger Charlottesville | 2018/10/27 14:00 | Petros Chrysochos v Oliver Crawford | 7-5,3-6,6-3 |
| ITF USA F28 | 2018/10/21 16:30 | Andrew Watson v Oliver Crawford | 1-6,1-6 |
| ITF USA F28 | 2018/10/20 14:00 | Jordi Arconada v Oliver Crawford | 4-6,0-6 |
| ITF USA F28 | 2018/10/19 15:00 | Maxime Cressy v Oliver Crawford | 4-6,6-1,3-6 |
| ITF USA F28 | 2018/10/18 17:50 | Oliver Crawford v Ronnie Schneider | 6-3,6-3 |
| ITF USA F28 | 2018/10/17 14:30 | Oliver Crawford v Jonathan Chang | 6-1,6-2 |
| Challenger Binghamton Qual | 2018/07/22 14:45 | Karue Sell v Oliver Crawford | 7-6,6-3 |