Stadium: Court 6 Round: 26 Ground: Clay
| Irpin, Singles Qualifying M-ITF-UKR-04A | 2019/08/13 06:30 | Ivan Sergeyev v Illya Beloborodko | 6-1,7-6 |
| ITF Panama F4 | 2018/11/21 14:00 | Ivan Sergeyev v Tikhomirov, Maksim | 7-6,7-5 |
| ITF Panama F4 | 2018/11/19 20:30 | Berry, Noah v Ivan Sergeyev | 1-6,2-6 |
| ITF Ukraine F4 | 2018/08/30 09:25 | Ivan Sergeyev v Petrone, Alessandro | 0-6,7-6,2-6 |
| ITF Ukraine F4 | 2018/08/29 14:30 | Khassanov, Roman v Ivan Sergeyev | 6-7,1-6 |
| ITF Ukraine F4 | 2018/08/28 12:05 | Ivan Sergeyev v Fekiac, Martin | 5-7,6-3,6-0 |
| ITF Ukraine F4 | 2018/08/27 07:00 | Curci, Matteo v Ivan Sergeyev | 3-6,2-6 |
| ITF Ukraine F4 | 2018/08/26 10:00 | Ivan Sergeyev v Luigi Sorrentino | 7-5,7-6 |
| Irpin, Singles Qualifying M-ITF-UKR-04A | 2019/08/13 09:45 | Solberg, Christoffer v Uspensky, Dennis | 4-6,0-6 |
| ITF M15 Telavi | 2019/07/28 12:00 | Uspensky, Dennis v Nikita Mashtakov | 3-6,4-6 |
| ITF M15 Telavi | 2019/07/27 06:00 | Uspensky, Dennis v Mikalai Haliak | 6-1,6-3 |
| ITF M15 Telavi | 2019/07/26 06:00 | Tashbulatov, Dostanbek v Uspensky, Dennis | 1-6,5-7 |
| ITF M15 Telavi | 2019/07/25 07:55 | Gorodynskyi, Vladyslav v Uspensky, Dennis | 1-6,0-6 |
| ITF M15 Telavi | 2019/07/24 06:00 | Chelidze, David v Uspensky, Dennis | 3-6,0-6 |
| ITF M15 Telavi | 2019/07/18 09:30 | Karimov, Jurabek v Uspensky, Dennis | 6-4,6-3 |
| ITF M15 Telavi | 2019/07/16 07:50 | Uspensky, Dennis v Nabiev, Olimjon | 6-1,6-3 |