Estádio: Court 9 Round: 26 Ground: Hardcourt indoor
| Challenger - Charlottesville | 2019/10/30 16:10 | Gianni Ross v Liam Caruana | 6-7,1-6 |
| Challenger - Charlottesville | 2019/10/29 14:00 | Roy Smith v Liam Caruana | 4-6,5-7 |
| Challenger - Charlottesville | 2019/10/28 14:00 | Liam Caruana v Cannon Kingsley | 6-3,7-6 |
| ITF - M25 Fayetteville | 2019/10/23 18:00 | Nick Chappell v Liam Caruana | 7-5,6-4 |
| ITF - M25 Waco | 2019/10/17 16:00 | Nick Chappell v Liam Caruana | 6-4,6-4 |
| ITF - M25 Waco | 2019/10/16 14:45 | Liam Caruana v Zachary Svajda | 6-3,6-3 |
| ITF - M25 Harlingen | 2019/09/28 01:00 | Alex Rybakov v Liam Caruana | 7-5,6-4 |
| ITF - M25 Harlingen | 2019/09/27 00:35 | Nathan Ponwith v Liam Caruana | 4-6,6-4,4-10 |
| Challenger - Charlottesville | 2019/10/30 17:45 | Raymond Sarmiento v Blaz Rola | 5-7,2-6 |
| Challenger - Las Vegas | 2019/10/15 20:55 | Blaz Rola v Stefan Kozlov | 4-6,3-6 |
| Challenger - Fairfield | 2019/10/10 17:00 | Darian King v Blaz Rola | 6-4,6-2 |
| Challenger - Fairfield | 2019/10/09 17:00 | Agustin Velotti v Blaz Rola | 1-6,4-6 |
| Challenger - Florença | 2019/09/26 11:55 | Blaz Rola v Mohamed Safwat | 4-6,7-5,4-6 |
| Challenger - Florença | 2019/09/25 10:00 | Blaz Rola v Oriol Roca Batalla | 6-7,6-4,7-5 |
| Challenger - Sibiu | 2019/09/20 11:05 | Alex Molcan v Blaz Rola | 6-4,6-7,6-4 |
| Challenger - Sibiu | 2019/09/19 11:40 | Pedja Krstin v Blaz Rola | 1-6,6-3,1-6 |