Stadium: Centre Court Round: 26
| ITF Panama F4 | 2018/11/19 20:30 | Noah Berry v Ivan Sergeyev | 1-6,2-6 |
| ITF Ukraine F4 | 2018/08/30 09:25 | Ivan Sergeyev v Alessandro Petrone | 0-6,7-6,2-6 |
| ITF Ukraine F4 | 2018/08/29 14:30 | Roman Khassanov v Ivan Sergeyev | 6-7,1-6 |
| ITF Ukraine F4 | 2018/08/28 12:05 | Ivan Sergeyev v Martin Fekiac | 5-7,6-3,6-0 |
| ITF Ukraine F4 | 2018/08/27 07:00 | Matteo Curci v Ivan Sergeyev | 3-6,2-6 |
| ITF Ukraine F4 | 2018/08/26 10:00 | Ivan Sergeyev v Luigi Sorrentino | 7-5,7-6 |
| Challenger Panama City Qual | 2018/03/31 14:30 | Alex Lawson v Ivan Sergeyev | 2-6,2-6 |
| ITF Ukraine F1 | 2017/05/11 07:00 | Ivan Sergeyev v Filip Horansky | 3-6,0-6 |
| ITF Panama F4 | 2018/11/19 14:00 | Sergio Luis H Ramirez v Maksim Tikhomirov | 3-6,3-6 |
| ITF Portugal F22 | 2018/10/23 14:20 | Maksim Tikhomirov v Gijs Brouwer | 2-6,1-6 |
| ITF Portugal F21 | 2018/10/17 10:40 | Maksim Tikhomirov v Miguel Semmler | 4-6,3-6 |
| ITF Portugal F21 | 2018/10/16 14:00 | Goncalo Falcao v Maksim Tikhomirov | 1-6,3-6 |
| ITF Portugal F20 | 2018/10/13 08:30 | Maksim Tikhomirov v Peter Goldsteiner | 3-6,6-3,5-7 |
| ITF Portugal F20 | 2018/10/12 10:00 | Maksim Tikhomirov v Franco Emanuel Egea | 5-7,6-4,6-3 |
| ITF Portugal F20 | 2018/10/11 17:00 | Maksim Tikhomirov v Pedro Araujo | 6-4,6-1 |
| ITF Portugal F20 | 2018/10/10 13:15 | Maksim Tikhomirov v Goncalo Ferreira | 6-0,6-4 |