Stadium: Sparkassen Court Round: 25 Ground: Clay
| German Championship | 2020/12/07 15:00 | Neo Niedner v Jim Walder | 2-6,6-4,6-7 |
| ITF M25 - Bakio | 2021/06/29 13:00 | Pablo Llamas Ruiz v Tobias Simon | 7-5,6-2 |
| ITF M25 - Klosters | 2021/06/24 08:35 | Dominic Stephan Stricker v Tobias Simon | 7-6,6-7,6-3 |
| ITF M25 - Klosters | 2021/06/23 12:00 | Tomas Papik v Tobias Simon | 3-6,4-6 |
| Challenger - Forli | 2021/06/14 09:30 | Thiago Agustin Tirante v Tobias Simon | 7-6,6-3 |
| Challenger - Forli | 2021/06/13 14:15 | Matteo Arnaldi v Tobias Simon | 6-7,2-6 |
| ITF M15 - Gaiba | 2021/06/11 10:00 | Benjamin Lock v Tobias Simon | 6-2,6-3 |
| ITF M15 - Gaiba | 2021/06/10 14:45 | Federico Bertuccioli v Tobias Simon | 4-6,3-6 |
| ITF M15 - Gaiba | 2021/06/09 15:55 | Andrea Picchione v Tobias Simon | 5-7,7-6,5-7 |