Stadium: Court 3 Round: 25 Ground: Clay
| ITF M25 Wroclaw | 2021/07/02 09:00 | Vladyslav Orlov v Oscar Jose Gutierrez | 1-6,1-6 |
| ITF M25 Wroclaw | 2021/07/01 08:55 | Vladyslav Orlov v Nicholas David Ionel | 6-2,3-6,6-3 |
| ITF M25 Wroclaw | 2021/06/29 15:20 | Vladyslav Orlov v Nicolas Moreno De Alboran | 6-4,6-2 |
| Challenger – Almatõ | 2021/06/15 06:00 | Tomas Barrios Vera v Vladyslav Orlov | 7-6,6-2 |
| Challenger – Almatõ | 2021/06/14 04:00 | Filip Cristian Jianu v Vladyslav Orlov | 6-7,1-6 |
| Challenger Almaty Qual | 2021/06/13 07:25 | Ivan Gakhov v Vladyslav Orlov | 6-7,6-7 |
| Challenger – Almatõ | 2021/06/08 09:15 | Vladyslav Orlov v Dmitry Popko | 2-6,3-6 |
| Challenger – Almatõ | 2021/06/07 05:00 | Jesper De Jong v Vladyslav Orlov | 4-6,1-6 |
| ITF M25 Marburg | 2021/07/07 12:30 | Daniel Cukierman v Milan Welte | 4-6,4-6 |
| ITF M25 Belgrade | 2021/07/04 07:55 | Nick Hardt v Daniel Cukierman | 3-6,6-3,6-3 |
| ITF M25 Belgrade | 2021/07/02 07:00 | Daniel Cukierman v Miljan Zekic | 6-4,6-4 |
| ITF M25 Belgrade | 2021/07/01 07:00 | Jaimee Floyd Angele v Daniel Cukierman | 6-3,4-6,4-6 |
| ITF M25 Belgrade | 2021/06/30 07:00 | Strahinja Rakic v Daniel Cukierman | 3-6,2-6 |
| ITF M25 Belgrade | 2021/06/29 07:00 | Daniel Cukierman v Mirko Martinez | 6-1,6-4 |
| ITF M25 Belgrade | 2021/06/28 07:00 | Daniel Cukierman v Vladislav Melnic | 6-3,6-1 |
| ITF M25 Belgrade | 2021/06/27 11:00 | Daniel Cukierman v Aleksa Bucan | 6-2,6-1 |