Stadium: Court 8 Round: 62 Ground: Clay
| Challenger Tampere | 2023/07/16 08:00 | Siim Troost v Lorenzo Rottoli | 3-6,3-6 |
| ITF M15 Monastir | 2023/06/26 08:00 | James Connel v Siim Troost | 6-4,6-3 |
| ITF M15 Monastir | 2023/06/25 08:30 | Ryan A Dos Santos v Siim Troost | 2-6,6-7 |
| ITF M15 Monastir | 2023/06/21 13:00 | Siim Troost v Cyril Vandermeersch | 3-6,5-7 |
| ITF M15 Monastir | 2023/06/19 14:00 | Gabriele Thomas Brancatelli v Siim Troost | 5-7,2-6 |
| ITF M15 Monastir | 2023/06/18 12:00 | Bryce Robinson v Siim Troost | 1-6,3-6 |
| Davis Cup | 2023/06/16 07:30 | Siim Troost v Filippo Tommesani | 6-1,6-1 |
| ITF M15 Vaasa | 2023/06/08 08:00 | Tom Gentzsch v Siim Troost | 6-3,6-3 |
| ITF M25 Telfs | 2023/07/17 07:00 | Nico Jaeger v Davide Galvanin | 7-6,7-6 |
| ITF M25 Telfs | 2023/07/16 07:00 | Davide Galvanin v Alfred Almasi | 4-6,7-5,10-6 |
| ITF M25 Cattolica | 2023/06/19 11:10 | Federico Marchetti v Davide Galvanin | 3-6,6-2,11-9 |
| ITF M25 Cattolica | 2023/06/18 14:30 | Davide Galvanin v Antonio Mazzeo | 7-5,6-1 |
| ITF M15 Doboj | 2023/05/08 08:00 | Vladislav Ivanov v Davide Galvanin | 6-4,7-6 |
| ITF M15 Doboj | 2023/05/07 08:00 | Davide Galvanin v Aldin Jasarevic | 6-0,6-2 |
| ITF M15 Porec | 2023/03/05 09:00 | Davide Galvanin v Alessio Zanotti | 1-6,2-6 |
| ITF M25 Monastir | 2023/02/12 12:30 | Mario G Fernandez v Davide Galvanin | 6-1,6-0 |