Stadium: Court 7 Round: 44 Ground: Clay
| 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 |
| 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 M25 Lodz | 2023/08/08 09:00 | Marcel Kamrowski v Kacper Szymkowiak | 6-4,7-5 |
| ITF M25 Lodz | 2023/08/07 13:30 | Dimitris Sakellaridis v Kacper Szymkowiak | 4-6,3-6 |
| ITF M25 Lodz | 2023/08/07 07:30 | Kacper Szymkowiak v Aliaksey Matsiush | 6-1,6-1 |
| ITF M15 Wroclaw | 2023/06/25 08:00 | Michael Minasyan v Kacper Szymkowiak | 6-4,1-6,1-10 |