Stadium: Court 1 Round: 26 Ground: Clay
| ITF - M25 Meerbusch | 2021/04/14 12:25 | Sebastian Prechtel v Tobias Simon | 5-7,6-3,3-6 |
| Challenger - Lille | 2021/03/21 13:55 | Tobias Simon v Edan Leshem | 2-6,6-7 |
| ITF - M15 Sharm El Sheikh | 2021/02/10 11:15 | Tobias Simon v Marek Gengel | 5-7,4-6 |
| ITF - M15 Sharm El Sheikh | 2021/02/04 10:10 | Tobias Simon v Marko Tepavac | 4-6,2-6 |
| ITF - M15 Sharm El Sheikh | 2021/02/03 12:50 | Tobias Simon v Remy Bertola | 6-2,6-4 |
| ITF - M15 Bressuire | 2021/01/20 09:30 | Corentin Denolly v Tobias Simon | 7-6,7-6 |
| ITF - M15 Manacor | 2021/01/16 12:15 | Evan Furness v Tobias Simon | 6-2,6-3 |
| ITF - M15 Manacor | 2021/01/15 09:15 | Matteo Martineau v Tobias Simon | 6-7,6-1,3-6 |
| ITF - M25 Meerbusch | 2021/04/14 10:00 | Tim Handel v Jiri Lehecka | 6-2,1-6,6-3 |
| ITF - M25 Meerbusch | 2021/04/12 12:00 | Tim Handel v Hazem Naw | 6-2,6-1 |
| ITF - M15 Sharm El Sheikh | 2021/03/28 08:00 | Daniel Cox v Tim Handel | 6-3,7-5 |
| ITF - M15 Sharm El Sheikh | 2021/03/23 09:10 | Tim Handel v Andres Gabriel Ciurletti | 6-7,4-6 |
| ITF - M15 Sharm El Sheikh | 2021/03/22 13:00 | Tim Handel v Ivan Mikhaylyuk | 6-3,6-1 |
| ITF - M15 Sharm El Sheikh | 2021/03/21 17:30 | Issei Okamura v Tim Handel | 4-6,4-6 |
| German Championship | 2020/12/11 13:00 | Tim Handel v Elmar Ejupovic | 1-6,1-6 |
| German Championship | 2020/12/10 14:00 | Tim Handel v Niklas Guttau | 7-6,7-6 |