Round: 44 Ground: Hardcourt outdoor
| ITF Ukraine F4 Qual | 2016/09/19 07:00 | Maksim Malyshev v Oleksander Kyrychenko | 6-1,6-1 |
| ITF Ukraine F2 | 2015/05/17 09:00 | Oleksander Kyrychenko v Maksim Malyshev | 6-2,4-6,6-4 |
| ITF Belarus F1 | 2014/10/13 07:00 | Maksim Malyshev v Oleksander Kyrychenko | 6-4,6-4 |
| ITF Ukraine F4 Qual | 2016/09/19 07:00 | Maksim Malyshev v Oleksander Kyrychenko | 6-1,6-1 |
| ITF Ukraine F4 Qual | 2016/09/18 09:30 | Oleksander Kyrychenko v Michal Kominek | 6-3,6-2 |
| ITF Ukraine F4 Qual | 2016/09/17 07:00 | Oleksander Kyrychenko v Dmitry Resnyanskiy | 6-2,6-2 |
| ITF Turkey F22 | 2016/05/29 11:30 | Joshua Paris v Oleksander Kyrychenko | 6-1,7-6 |
| ITF Ukraine F2 | 2016/05/19 08:30 | Lukas Mugevicius v Oleksander Kyrychenko | 7-5,4-6,6-0 |
| ITF Ukraine F2 | 2016/05/16 07:00 | Oleksander Kyrychenko v Anatoliy Petrenko | 6-4,7-6 |
| ITF Ukraine F2 | 2016/05/15 08:00 | Vladyslav Orlov v Oleksander Kyrychenko | 4-6,1-6 |
| ITF Ukraine F1 | 2016/05/09 06:30 | Anatoliy Petrenko v Oleksander Kyrychenko | 6-2,6-0 |
| ITF Ukraine F5 | 2016/09/28 08:30 | Denis Yevseyev v Maksim Malyshev | 6-4,6-1 |
| ITF Ukraine F5 | 2016/09/27 08:30 | Olexiy Kolisnyk v Maksim Malyshev | 1-6,1-6 |
| ITF Ukraine F5 | 2016/09/26 07:00 | Tadas Tarasevicius v Maksim Malyshev | 3-6,6-3,4-6 |
| ITF Ukraine F5 | 2016/09/25 09:30 | Mateusz Piatek v Maksim Malyshev | 0-6,1-6 |
| ITF Ukraine F4 | 2016/09/21 07:00 | Daniil Zarichanskiy v Maksim Malyshev | 6-4,6-2 |
| ITF Ukraine F4 Qual | 2016/09/19 07:00 | Maksim Malyshev v Oleksander Kyrychenko | 6-1,6-1 |
| ITF Belarus F1 | 2016/08/09 09:55 | Maksim Malyshev v Aleksandr Malyshev | 4-6,3-6 |
| ITF Belarus F1 Qual | 2016/08/07 08:00 | Maksim Malyshev v Dmitry Resnyanskiy | 6-0,6-3 |