Stadium: Court 3 Round: 25 Ground: Clay
| ITF M25 Caslano | 2021/08/24 07:30 | Stefano Baldoni v Carlo Alberto Fossati | 6-2,6-3 |
| ITF M25 Caslano | 2021/08/23 11:55 | Stefano Baldoni v Jimmy Yang | 4-6,6-4,10-8 |
| ITF M15 Pescara | 2021/08/15 07:15 | Stefano Baldoni v Fausto Tabacco | 3-6,2-6 |
| ITF M15 Cairo | 2020/12/02 10:40 | Erik Crepaldi v Stefano Baldoni | 6-4,2-6,6-3 |
| ITF M15 Cairo | 2020/12/01 08:00 | Luis Patino v Stefano Baldoni | 3-6,6-7 |
| ITF M15 Cairo | 2020/11/30 08:00 | Stefano Baldoni v Anirudh Chandrasekar | 6-0,6-4 |
| ITF M15 Cairo | 2020/11/29 07:00 | Fares Zakaria v Stefano Baldoni | 0-6,2-6 |
| ITF M15 Cairo | 2020/11/25 10:50 | Stefano Baldoni v Aldin Setkic | 4-6,2-6 |
| 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 |
| ITF M15 Gaiba | 2021/06/10 14:45 | Federico Bertuccioli v Tobias Simon | 4-6,3-6 |