Stadium: Court 1 Round: 25 Ground: Clay
| ITF M25 - Meerbusch | 2021/04/15 13:25 | Tobias Simon v Tim Handel | 4-6,6-7 |
| 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 - Valldoreix | 2021/05/10 11:00 | Federico Iannaccone v Yan Bondarevskiy | 2-6,7-6,6-10 |
| ITF M15 - Valldoreix | 2021/05/09 14:00 | Michiel de Krom v Federico Iannaccone | 3-6,2-6 |
| ITF M15 - Majadahonda | 2021/05/02 14:45 | Federico Iannaccone v Pedro Araujo | 1-6,6-7 |
| ITF M15 - LPD Gran Canaria | 2021/04/29 13:55 | Kyrian Jacquet v Federico Iannaccone | 6-2,6-1 |
| ITF M15 - LPD Gran Canaria | 2021/04/28 14:40 | Aaron Cohen v Federico Iannaccone | 3-6,3-6 |
| ITF M15 Las Palmas | 2021/04/27 08:00 | Federico Iannaccone v Albert Roglan | 6-3,6-1 |
| ITF M15 Las Palmas | 2021/04/26 09:30 | Federico Iannaccone v Joan B B Isern | 6-3,6-3 |
| ITF M25 - Biel | 2021/03/29 11:00 | Alexis Gautier v Federico Iannaccone | 5-7,6-0,10-7 |