Stadium: Court 1 Round: 1
| International Tennis Series | 2020/06/23 12:00 | Caleb Strother v Enzo Wallart | 1-6,2-6 |
| International Tennis Series | 2020/06/22 15:30 | Stefan Storch v Caleb Strother | 6-1,6-2 |
| International Tennis Series | 2020/06/22 12:00 | Mitchell Johnson v Caleb Strother | 6-1,6-0 |
| ITF M25 Naples | 2020/02/09 15:00 | Maciej Smola v Caleb Strother | 6-1,6-0 |
| ITF M15 Tallahassee | 2019/12/02 15:00 | Caleb Strother v Daniel Labrador | 2-6,2-6 |
| ITF USA F4 | 2018/01/12 14:30 | Grigoriy Lomakin v Caleb Strother | 6-4,6-3 |
| ITF USA F9 | 2017/02/24 15:00 | Caleb Strother v Mac Kiger | 0-6,0-6 |