Stadium: N5 Round: 26 Ground: Hardcourt outdoor
| 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 USA F28 | 2018/10/21 16:30 | Andrew Watson v Oliver Crawford | 1-6,1-6 |
| ITF M25 Champaign | 2019/07/24 17:00 | Errol Smith v Kyle Seelig | 7-6,6-4 |
| ITF M25 Iowa City | 2019/07/19 16:15 | Axel Geller v Errol Smith | 2-6,6-3,6-0 |
| ITF M25 Iowa City | 2019/07/18 14:00 | Errol Smith v Alejandro Gonzalez | 7-6,6-4 |
| ITF M25 Iowa City | 2019/07/17 16:30 | Alfredo Perez v Errol Smith | 5-7,7-6,6-7 |
| ITF M15 Pittsburgh | 2019/07/03 16:30 | Errol Smith v Ricardo Rodriguez-Pace | 4-6,0-6 |
| ITF M15 Rochester | 2019/06/26 18:45 | Kyle Seelig v Errol Smith | 6-2,6-2 |
| ITF M15 Cancun | 2019/06/13 13:30 | Errol Smith v Hady Habib | 6-7,4-6 |
| ITF M15 Cancun | 2019/06/12 15:55 | Mwendwa Mbithi v Errol Smith | 4-6,6-7 |