Stadium: Court 1 Round: 26 Ground: Clay
| ITF M25 Prague | 2021/10/06 12:20 | Simon, Tobias v Matthew William Donald | 6-3,4-6,6-3 |
| ITF M25 Falun | 2021/09/28 13:15 | Simon, Tobias v Daniel Little | 6-7,3-6 |
| Challenger Biel | 2021/09/20 09:00 | Simon, Tobias v Jakub Paul | 4-6,4-6 |
| Challenger Biel | 2021/09/19 11:15 | Laurent Lokoli v Simon, Tobias | 4-6,2-6 |
| ITF M25 Plaisir | 2021/09/15 14:05 | Briand, Jurgen v Simon, Tobias | 6-4,7-6 |
| Challenger Tulln | 2021/09/06 10:25 | Ignatik, Uladzimir v Simon, Tobias | 6-4,4-6,7-5 |
| Challenger Tulln | 2021/09/05 13:00 | Matos, Rafael v Simon, Tobias | 6-7,2-6 |
| ITF M25 Caslano | 2021/08/26 14:30 | Giovanni Oradini v Simon, Tobias | 4-6,6-4,3-6 |
| ITF M25 Prague | 2021/10/06 10:15 | Dominik Kellovsky v Milos Karol | 5-7,4-6 |
| ITF M25 Prague | 2021/10/04 12:20 | Milos Karol v Matyas Cerny | 7-6,7-5 |
| ITF M25 Prague | 2021/10/03 13:00 | Milos Karol v Vitek Horak | 6-0,6-1 |
| ITF M25 Budapest | 2021/09/30 09:00 | Milos Karol v Mate Valkusz | 6-7,0-6 |
| ITF M25 Budapest | 2021/09/29 07:25 | Mark Havlicek v Milos Karol | 2-6,7-6,4-6 |
| ITF M25 Pardubice | 2021/09/23 11:15 | Milos Karol v Henri Squire | 1-6,1-6 |
| ITF M15 Zilina | 2021/09/01 10:00 | Milos Karol v Podzus, Martins | 3-6,6-4,1-6 |
| ITF M15 Bratislava | 2021/08/16 10:30 | Tomas Lanik v Milos Karol | 4-6,7-5,12-10 |