Stadium: Court 1 Round: 25 Ground: Hardcourt outdoor
| ITF - M25 Hamburg | 2021/10/21 08:00 | Daniel Little v Vladyslav Orlov | 7-5,6-1 |
| ITF - M25 Hamburg | 2021/10/19 10:55 | Tom Schonenberg v Vladyslav Orlov | 3-6,6-7 |
| Challenger - Alicante | 2021/10/11 14:30 | Vladyslav Orlov v Mischa Zverev | 2-6,1-6 |
| Challenger - Barcelona | 2021/10/03 08:00 | Georgii Kravchenko v Vladyslav Orlov | 6-4,6-1 |
| Challenger - Bukurešť | 2021/09/19 11:35 | Dragos Nicolae Madaras v Vladyslav Orlov | 3-6,6-1,6-0 |
| Challenger - Kyjev | 2021/09/06 09:45 | Vladyslav Orlov v Clement Tabur | 1-6,6-1,3-6 |
| Challenger - Kyjev | 2021/09/05 09:30 | Vladyslav Orlov v Yan Bondarevskiy | 7-5,6-2 |
| Challenger - Barletta | 2021/08/22 14:00 | Vladyslav Orlov v Luca Potenza | 4-6,6-4,5-7 |
| ITF - M25 Quinta Do Lago | 2021/10/20 12:35 | Tiago Cacao v Arthur Cazaux | 6-7,2-6 |
| ITF - M25 Loule | 2021/10/12 13:00 | Tiago Cacao v Luis Faria | 3-6,6-4,0-6 |
| ITF - M25 Setubal | 2021/10/06 12:20 | Tiago Cacao v Maximilian Neuchrist | 6-7,0-6 |
| Challenger - Lisabon | 2021/09/28 15:55 | Joao Domingues v Tiago Cacao | 6-4,6-4 |
| Challenger - Braga | 2021/09/22 12:00 | Thiago Monteiro v Tiago Cacao | 6-1,6-1 |
| Challenger - Braga | 2021/09/20 11:30 | Tiago Cacao v Roberto Ortega-Olmedo | 4-6,6-1,6-1 |
| ITF - M25 Sintra | 2021/09/14 17:35 | Alejandro Moro Canas v Tiago Cacao | 6-1,7-5 |
| Challenger - Praha | 2021/08/23 11:00 | Tiago Cacao v Facundo Diaz Acosta | 4-6,0-6 |