Stadium: N2 Round: 27 Ground: Hardcourt outdoor
| ITF M25 Champaign | 2019/07/25 19:45 | Oliver Crawford v Errol Smith | 4-6,6-1,6-1 |
| ITF M25 Champaign | 2019/07/24 17:00 | Oliver Crawford v Ricardo Rodriguez-Pace | 6-3,6-2 |
| ITF M25 Wichita | 2019/06/14 17:15 | Brandon Holt v Oliver Crawford | 6-4,6-4 |
| ITF M25 Wichita | 2019/06/13 17:25 | Alexander Lebedev v Oliver Crawford | 3-6,1-6 |
| ITF M25 Wichita | 2019/06/11 18:15 | David Fox v Oliver Crawford | 3-6,1-6 |
| Challenger Little Rock | 2019/06/05 18:40 | Darian King v Oliver Crawford | 6-4,6-4 |
| 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 M25 Champaign | 2019/07/25 21:55 | Alec Adamson v Ruan Roelofse | 7-6,4-6,5-7 |
| ITF M25 Champaign | 2019/07/24 19:05 | Juan Carlos Aguilar v Ruan Roelofse | 2-6,5-7 |
| ITF M15 Saarlouis | 2019/07/03 10:00 | Luca Gelhardt v Ruan Roelofse | 7-5,6-3 |
| ITF M25 Palma del Rio | 2019/06/29 20:35 | Ruan Roelofse v Arthur Rinderknech | 2-6,3-6 |
| ITF M25 Palma del Rio | 2019/06/28 20:30 | John Echeverria v Ruan Roelofse | 6-7,6-4,3-6 |
| ITF M25 Palma del Rio | 2019/06/27 20:00 | Ruan Roelofse v Eduardo Struvay | 6-3,6-7,7-6 |
| ITF M25 Palma del Rio | 2019/06/25 16:30 | Ruan Roelofse v Jose Antonio Dugo Reyes | 6-2,7-5 |
| ITF M25 Martos | 2019/06/20 13:00 | Benjamin Winter Lopez v Ruan Roelofse | 6-2,6-3 |