Stadium: Court 1 Round: 27 Ground: Clay
| Challenger Tulln | 2021/09/06 10:25 | Uladzimir Ignatik v Tobias Simon | 6-4,4-6,7-5 |
| ITF M25 Prague | 2021/10/07 14:05 | Tobias Simon v Milos Karol | 6-4,4-6,7-6 |
| ITF M25 Prague | 2021/10/06 12:20 | Tobias Simon v Matthew William Donald | 6-3,4-6,6-3 |
| ITF M25 Falun | 2021/09/28 13:15 | Tobias Simon v Daniel Little | 6-7,3-6 |
| Challenger Biel | 2021/09/20 09:00 | Tobias Simon v Jakub Paul | 4-6,4-6 |
| Challenger Biel | 2021/09/19 11:15 | Laurent Lokoli v Tobias Simon | 4-6,2-6 |
| ITF M25 Plaisir | 2021/09/15 14:05 | Jurgen Briand v Tobias Simon | 6-4,7-6 |
| Challenger Tulln | 2021/09/06 10:25 | Uladzimir Ignatik v Tobias Simon | 6-4,4-6,7-5 |
| Challenger Tulln | 2021/09/05 13:00 | Rafael Matos v Tobias Simon | 6-7,2-6 |
| ITF M25 Prague | 2021/10/07 09:20 | Danylo Kalenichenko v Uladzimir Ignatik | 3-6,6-3,3-6 |
| ITF M25 Prague | 2021/10/06 08:55 | Stepan Pecak v Uladzimir Ignatik | 3-6,3-6 |
| Challenger Sibiu | 2021/09/26 07:30 | Uladzimir Ignatik v Oleg Prihodko | 3-6,3-6 |
| Challenger Bucharest | 2021/09/20 08:00 | Ivan Gakhov v Uladzimir Ignatik | 0-6,6-2,6-3 |
| Challenger Bucharest | 2021/09/19 09:45 | David Poljak v Uladzimir Ignatik | 4-6,1-6 |
| Challenger Tulln | 2021/09/07 15:35 | Dennis Novak v Uladzimir Ignatik | 1-6,6-4,6-2 |
| Challenger Tulln | 2021/09/06 10:25 | Uladzimir Ignatik v Tobias Simon | 6-4,4-6,7-5 |
| Challenger Tulln | 2021/09/05 12:25 | Uladzimir Ignatik v David Pichler | 6-2,6-3 |