Stadium: Court 1 Round: 25 Ground: Clay
| 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 Caslano | 2021/08/26 14:30 | Giovanni Oradini v Tobias Simon | 4-6,6-4,3-6 |
| ITF M25 Caslano | 2021/08/25 13:10 | Stefano Baldoni v Tobias Simon | 6-7,1-6 |
| ITF M25 Pardubice | 2021/09/23 11:15 | Matthew William Donald v Luca Nardi | 4-6,3-6 |
| ITF M25 Pardubice | 2021/09/22 09:00 | Tomas Lanik v Matthew William Donald | 2-6,2-6 |
| ITF M25 Prostejov | 2021/08/16 11:15 | Zsombor Piros v Matthew William Donald | 6-3,6-4 |
| Challenger Liberec | 2021/08/01 14:00 | Matthew William Donald v Rudolf Molleker | 6-4,5-7,5-7 |
| ITF M25 Jablonec Nad Nisou | 2021/05/19 15:15 | Matthew William Donald v Manuel Guinard | 1-6,5-7 |
| ITF M25 Prague | 2021/05/09 12:30 | Matthew William Donald v Lenny Hampel | 2-6,6-4,8-10 |