Stadium: Court 28 Round: 54 Ground: Clay
| International Tennis Series | 2020/06/24 15:20 | Sean Burnette v Caleb Strother | 6-2,6-0 |
| International Tennis Series | 2020/06/23 15:35 | Sean Burnette v Caleb Strother | 6-4,6-4 |
| 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 - Naples M25 | 2020/02/09 15:00 | Maciej Smola v Caleb Strother | 6-1,6-0 |
| ITF - Tallahassee M15 | 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 M25 Fayetteville | 2020/11/02 17:30 | Joshua Sheehy v Oscar Mesquida Berg | 7-6,3-6,10-8 |
| ITF - Cancun M15 | 2020/03/11 14:00 | Maximiliano Estevez v Oscar Mesquida Berg | 6-2,6-3 |
| ITF - Cancun M15 | 2020/03/09 15:00 | Felipe M Sarrasague v Oscar Mesquida Berg | 4-6,3-6 |
| ITF - Cancun M15 | 2020/03/09 14:00 | Toby D. Boyer v Oscar Mesquida Berg | 3-6,2-6 |
| ITF - Cancun M15 | 2020/03/08 14:30 | Jabari Stafford v Oscar Mesquida Berg | 0-6,0-6 |
| ITF - Manacor M15 | 2020/01/13 12:00 | Ugo Blanchet v Oscar Mesquida Berg | 2-6,6-4,10-4 |
| ITF - Manacor M15 | 2020/01/12 10:00 | Pol Sanchez Vinas v Oscar Mesquida Berg | 6-7,3-6 |
| ITF - Manacor M15 | 2020/01/06 12:00 | Sacha Modica v Oscar Mesquida Berg | 7-5,1-6,10-6 |