Stadium: Citta Di Forlì Round: 14 Ground: Clay
| Challenger Forli | 2021/12/09 11:35 | Maxime Cressy v Matteo Gigante | 7-6,6-2 |
| Challenger Forli | 2021/12/07 15:20 | Marek Gengel v Matteo Gigante | 2-6,6-3,2-6 |
| Challenger Forli | 2021/11/30 15:30 | Jelle Sels v Matteo Gigante | 7-6,6-2 |
| Challenger Bari | 2021/11/22 10:10 | Sebastian Fanselow v Matteo Gigante | 2-6,7-5,6-2 |
| Challenger Bari | 2021/11/21 12:55 | Matteo Gigante v Lorenzo Bocchi | 6-2,7-6 |
| ITF M15 Selva Gardena | 2021/10/28 11:00 | Matteo Gigante v Leandro Riedi | 4-6,4-6 |
| ITF M15 Selva Gardena | 2021/10/27 15:30 | Matteo Gigante v Michael Gloeckler | 7-6,6-4 |
| ITF M15 Selva Gardena | 2021/10/26 07:30 | Martin Krumich v Matteo Gigante | 4-6,6-7 |
| Challenger Manama | 2021/11/22 08:00 | Tobias Simon v Maximilian Neuchrist | 3-6,6-4,3-6 |
| Challenger Manama | 2021/11/21 08:00 | Tobias Simon v Eric Vanshelboim | 4-6,6-3,6-0 |
| Challenger Ortisei | 2021/11/09 10:20 | Matthias Bachinger v Tobias Simon | 6-3,6-7,7-6 |
| Challenger Ortisei | 2021/11/08 09:30 | Tobias Simon v Filip Misolic | 7-5,7-6 |
| Challenger Ortisei | 2021/11/07 09:30 | Francesco Forti v Tobias Simon | 4-6,6-7 |
| Challenger Eckental | 2021/11/02 11:05 | Ruben Bemelmans v Tobias Simon | 6-7,6-3,7-5 |
| Challenger Eckental | 2021/11/01 11:55 | Tobias Simon v Peter Heller | 6-2,6-4 |
| Challenger Eckental | 2021/10/31 11:55 | Otto Virtanen v Tobias Simon | 1-6,4-6 |