Estádio: Court 5 Round: 25 Ground: Clay
| ITF - M15 Vejle | 2023/07/24 12:00 | Simon Freund v Henrik Bladelius | 6-1,6-1 |
| ITF - M15 Kalmar | 2023/05/16 12:00 | Simon Freund v Lewie Lane | 6-7,3-6 |
| ITF - M25 Värnamo | 2023/05/11 08:15 | Dragos Nicolae Madaras v Simon Freund | 6-1,6-4 |
| ITF - M25 Värnamo | 2023/05/10 08:10 | Simon Freund v Yan Sabanin | 6-0,6-0 |
| ITF - M15 Antália | 2023/04/24 09:05 | Simon Freund v Radovan Michalik | 2-6,0-6 |
| ITF - M15 Antália | 2023/04/17 12:35 | Konstantin Zhzhenov v Simon Freund | 1-6,6-2,10-2 |
| ITF - M15 Antália | 2023/04/16 07:00 | Maximilian Figl v Simon Freund | 6-1,2-6,5-10 |
| ITF - M15 Monastir | 2023/02/22 12:35 | Simon Freund v Niccolo Baroni | 7-5,4-6,2-6 |
| ITF - M15 Vejle | 2023/07/24 12:00 | Andrea Gola v Ivan Sergeyev | 7-5,6-4 |
| ITF - M15 Uslar | 2023/07/17 08:00 | Andrea Gola v Justin Engel | 2-6,3-6 |
| ITF - M25 Uriage | 2023/07/10 12:00 | Andrea Gola v Cesar Bouchelaghem | 3-6,3-6 |
| ITF - M25 Uriage | 2023/07/10 07:00 | Andrea Gola v Guillaume Majcher | 6-1,6-1 |
| ITF - M15 Duffel | 2023/06/15 10:00 | Ryan Nijboer v Andrea Gola | 2-6,6-1,6-3 |
| ITF - M15 Duffel | 2023/06/13 08:00 | Otakar Ungerman v Andrea Gola | 4-6,3-6 |
| ITF - M15 Duffel | 2023/06/12 08:00 | Andrea Gola v David Quayle | 6-1,6-2 |
| Challenger - Turim | 2023/05/15 10:35 | Federico Gaio v Andrea Gola | 6-2,6-3 |