Stadium: Court 1 - Center Round: 26 Ground: Clay
| ITF M25 Caslano | 2021/08/25 10:45 | Giovanni Oradini v Louroi Martinez | 6-3,2-6,6-2 |
| ITF M25 Caslano | 2021/08/24 11:35 | Giovanni Oradini v Caspar Schuetze | 6-4,6-0 |
| ITF M25 Caslano | 2021/08/23 09:50 | Giovanni Oradini v Raffael Schaer | 4-6,7-5,10-8 |
| ITF M15 Pescara | 2021/08/18 08:45 | Giovanni Oradini v Emiliano Maggioli | 3-6,4-6 |
| ITF M15 Pescara | 2021/08/16 13:00 | Giannicola Misasi v Giovanni Oradini | 1-6,6-3,2-10 |
| ITF M15 Pescara | 2021/08/16 07:15 | Theo Arribage v Giovanni Oradini | 3-6,1-6 |
| ITF M15 Pescara | 2021/08/15 07:00 | Francesco Liucci v Giovanni Oradini | 0-6,6-4,9-11 |
| ITF M25 Frankfurt am Main | 2021/08/11 08:55 | Giovanni Oradini v Alejandro Gomez | 2-6,4-6 |
| ITF M25 Caslano | 2021/08/25 13:10 | Stefano Baldoni v Tobias Simon | 6-7,1-6 |
| ITF M25 Frankfurt am Main | 2021/08/10 13:55 | Tobias Simon v Christian Sigsgaard | 3-6,3-6 |
| 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 |