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