Stadium: Court 5 Round: 25 Ground: Hardcourt outdoor
| Challenger Columbus 3 | 2019/09/17 14:00 | Jacob Dunbar v Ryan Shane | 5-7,4-6 |
| Challenger Columbus 3 | 2019/09/16 15:00 | Jacob Dunbar v Aleksandar Kovacevic | 4-6,6-3,6-2 |
| ITF M25 Memphis | 2019/08/14 23:00 | Kevin King v Jacob Dunbar | 1-6,6-4,6-3 |
| ITF M25 Memphis | 2019/08/13 20:10 | Takanyi Garanganga v Jacob Dunbar | 3-6,1-6 |
| ITF M25 Edwardsville | 2019/08/09 16:30 | Jacob Dunbar v Nathan Ponwith | 6-4,4-6,5-7 |
| ITF M25 Edwardsville | 2019/08/08 15:00 | Jacob Dunbar v Gianni Ross | 6-2,6-0 |
| ITF M25 Edwardsville | 2019/08/07 16:10 | Ryan Shane v Jacob Dunbar | 2-6,2-6 |
| ITF M25 Decatur | 2019/08/01 15:00 | Santiago Rodriguez Taverna v Jacob Dunbar | 6-3,1-6,7-6 |
| ITF M25 Waco | 2019/10/16 20:10 | Vasil Kirkov v Ben Patael | 4-6,1-6 |
| ITF M25 Waco | 2019/10/15 19:25 | Eric Morris v Vasil Kirkov | 0-6,1-6 |
| ITF M25 Waco | 2019/10/14 17:00 | Alastair Gray v Vasil Kirkov | 4-6,4-6 |
| ITF M25 Waco | 2019/10/13 17:30 | Herbert Jody Maginley v Vasil Kirkov | 1-6,6-4,8-10 |
| ITF M15 Cancun | 2019/08/27 14:10 | Vasil Kirkov v Hillel Rousseau | 6-3,6-4 |
| Challenger Lexington | 2019/07/31 17:50 | Vasil Kirkov v Akira Santillan | 4-6,3-6 |
| Challenger Lexington | 2019/07/30 14:30 | Ryan Shane v Vasil Kirkov | 3-6,6-1,3-6 |
| ITF M15 Rochester | 2019/06/26 23:05 | Strong Kirchheimer v Vasil Kirkov | 6-4,6-1 |