Stadium: Court 4 Round: 25 Ground: Clay
| ITF M25 Poznan | 2023/08/22 09:00 | Juliusz Bienkiewicz v Siim Troost | 6-2,3-6,10-4 |
| ITF M25 Poznan | 2023/08/21 11:30 | Michal Matuszewski v Siim Troost | 6-7,1-6 |
| ITF M25 Bielsko Biala | 2023/08/17 13:30 | Juan Bautista Torres v Siim Troost | 6-2,7-5 |
| ITF M25 Bielsko Biala | 2023/08/16 15:25 | Siim Troost v Jakub Jedrzejczak | 6-3,3-6,7-5 |
| 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 Koksijde | 2023/08/14 12:00 | Kai Wehnelt v Luciano Emanuel Ambrogi | 3-6,3-6 |
| Challenger Meerbusch | 2023/08/07 10:00 | Georgii Kravchenko v Kai Wehnelt | 6-4,7-6 |
| Challenger Luedenscheid | 2023/07/31 15:25 | Duje Ajdukovic v Kai Wehnelt | 6-4,3-6,6-3 |
| Challenger Luedenscheid | 2023/07/30 12:05 | Kai Wehnelt v Jose Pereira | 6-2,6-4 |
| ITF M25 Kramsach | 2023/07/27 13:45 | Kai Wehnelt v Peter Heller | 5-7,4-6 |
| ITF M25 Kramsach | 2023/07/26 12:20 | Kai Wehnelt v Manuel Plunger | 6-3,3-6,6-2 |
| ITF M25 Telfs | 2023/07/20 08:55 | Alex Barrena v Kai Wehnelt | 6-3,6-1 |
| ITF M25 Telfs | 2023/07/19 10:00 | Kai Wehnelt v Petro Orlando Fellin | 6-3,6-1 |