Stadium: Court 9 Round: 25 Ground: Hardcourt indoor
| Challenger Charlottesville | 2019/10/28 23:15 | Raymond Sarmiento v Liam Broady | 6-4,6-2 |
| ITF M25 Claremont | 2019/10/12 20:50 | Michael Geerts v Raymond Sarmiento | 6-4,7-6 |
| ITF M25 Claremont | 2019/10/11 18:00 | Raymond Sarmiento v Tanner K Smith | 6-4,7-6 |
| ITF M25 Claremont | 2019/10/10 20:45 | Raymond Sarmiento v Alexander Cozbinov | 6-2,6-3 |
| ITF M25 Claremont | 2019/10/09 21:20 | Christian Langmo v Raymond Sarmiento | 2-6,3-6 |
| Challenger Tiburon | 2019/09/23 22:05 | Brandon Holt v Raymond Sarmiento | 6-4,6-7,6-3 |
| Challenger New Haven | 2019/09/03 16:35 | John McNally v Raymond Sarmiento | 3-6,7-6,6-4 |
| ATP Winston-Salem | 2019/08/19 20:30 | Raymond Sarmiento v Jeremy Chardy | 1-6,6-7 |
| 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 Florence | 2019/09/26 11:55 | Blaz Rola v Mohamed Safwat | 4-6,7-5,4-6 |
| Challenger Florence | 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 |
| Challenger Sibiu | 2019/09/18 08:20 | Fabien Reboul v Blaz Rola | 3-6,6-4,3-6 |