Stadium: Court Center Round: 45 Ground: Clay
| Challenger Manama | 2021/11/22 13:15 | Geoffrey Blancaneaux v Ivan Marrero Curbelo | 6-3,6-2 |
| Challenger Tenerife | 2021/10/31 14:50 | Ivan Marrero Curbelo v Alexander Shevchenko | 3-6,2-6 |
| UTR Pro Tennis Series Mulheim | 2021/10/17 07:00 | Yurii Dzhavakian v Ivan Marrero Curbelo | 6-1,7-5 |
| UTR Pro Tennis Series Mulheim | 2021/10/16 12:00 | Alen Moritz Hodzic v Ivan Marrero Curbelo | 6-3,4-6,6-6 |
| UTR Pro Tennis Series Mulheim | 2021/10/14 07:00 | Ivan Marrero Curbelo v Benjamin Dhoe | 2-6,6-3,2-6 |
| UTR Pro Tennis Series Mulheim | 2021/10/13 10:20 | Ivan Marrero Curbelo v Diego Balderas | 6-1,5-1 |
| UTR Pro Tennis Series Mulheim | 2021/10/12 07:00 | Ivan Marrero Curbelo v Johann Willems | 2-6,3-5 |
| UTR Pro Tennis Series Mulheim | 2021/10/11 10:00 | Ivan Marrero Curbelo v Eric Vanshelboim | 1-6,0-6 |
| Challenger Antalya | 2021/12/07 07:30 | Georgii Kravchenko v Vladyslav Orlov | 4-6,1-6 |
| Challenger Antalya | 2021/11/29 11:05 | Oliver Crawford v Vladyslav Orlov | 6-3,6-4 |
| Challenger Antalya | 2021/11/29 07:00 | Koray Kirci v Vladyslav Orlov | 3-6,6-7 |
| Challenger Manama | 2021/11/23 13:00 | Vladyslav Orlov v Ramkumar Ramanathan | 2-6,4-6 |
| Challenger Manama | 2021/11/22 09:55 | Vladyslav Orlov v Michail Pervolarakis | 1-6,6-4,6-0 |
| Challenger Manama | 2021/11/21 09:55 | Vladyslav Orlov v Patrik Niklas-Salminen | 6-1,7-6 |
| Challenger Roanne | 2021/11/09 12:05 | Mathias Bourgue v Vladyslav Orlov | 6-3,6-2 |
| Challenger Roanne | 2021/11/08 12:25 | Gabriel Debru v Vladyslav Orlov | 6-3,6-4 |