Stadium: Center Court Round: 25 Ground: Clay
| ITF M25 Bielsko Biala | 2023/08/14 12:00 | Siim Troost v Patrik Homola | 4-6,5-7 |
| ITF M25 Bielsko Biala | 2023/08/14 07:30 | Siim Troost v Kacper Szymkowiak | 7-5,6-4 |
| ITF M25 Lodz | 2023/08/07 10:30 | Siim Troost v Piotr Grynkowski | 6-7,6-7 |
| ITF M15 Hyvinkaa | 2023/07/31 09:30 | Hermanni Tiainen v Siim Troost | 6-0,6-7,10-8 |
| ITF M25 Kramsach | 2023/07/24 11:30 | Siim Troost v Lambert Ruland | 2-6,4-6 |
| ITF M25 Kramsach | 2023/07/24 07:30 | Siim Troost v Lukas Rohseano | 4-6,6-4,10-8 |
| ITF M25 Kramsach | 2023/07/23 07:00 | Siim Troost v Davide Galvanin | 7-5,6-2 |
| Challenger Tampere | 2023/07/16 08:00 | Siim Troost v Lorenzo Rottoli | 3-6,3-6 |