Stadium: Court 1 Round: 25 Ground: Hardcourt indoor
| ITF M15 Heraklion | 2019/11/23 08:00 | Vasil Kirkov v Mick Veldheer | 6-4,5-7,1-6 |
| ITF M15 Heraklion | 2019/11/22 09:30 | Vasil Kirkov v Lenny Hampel | 7-6,4-6,6-3 |
| ITF M15 Heraklion | 2019/11/20 12:20 | Aristotelis Thanos v Vasil Kirkov | 4-6,2-6 |
| ITF M15 Heraklion | 2019/11/15 08:00 | Jan Zielinski v Vasil Kirkov | 6-3,6-3 |
| ITF M15 Heraklion | 2019/11/13 08:00 | Vasil Kirkov v Petros Tsitsipas | 7-6,7-6 |
| ITF M25 Fayetteville | 2019/10/23 20:15 | Jacob Dunbar v Vasil Kirkov | 3-6,6-2,6-1 |
| 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 |
| Challenger Charlottesville | 2019/10/31 15:00 | Dennis Novikov v Taro Daniel | 4-6,2-6 |
| Challenger Charlottesville | 2019/10/30 21:45 | Dennis Novikov v Alexander Ritschard | 6-2,6-1 |
| Challenger Charlottesville | 2019/10/28 14:00 | Dennis Novikov v Jacob Dunbar | 7-5,1-6,5-7 |
| Challenger Las Vegas | 2019/10/15 17:30 | Dennis Novikov v Ernesto Escobedo | 3-6,4-6 |
| Challenger Las Vegas | 2019/10/14 18:00 | Dennis Novikov v Ruan Roelofse | 6-3,6-4 |
| Challenger Fairfield | 2019/10/09 21:25 | Dennis Novikov v Brandon Nakashima | 2-6,4-6 |
| Challenger Fairfield | 2019/10/07 17:00 | Dennis Novikov v Sem Verbeek | 2-6,6-7 |
| Challenger Columbus 3 | 2019/09/17 18:45 | Dennis Novikov v Sekou Bangoura | 6-7,6-7 |