Stadium: Court 4 Round: 25 Ground: Clay
| 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 M15 Vaasa | 2023/06/07 08:50 | Siim Troost v Tuomas Rikkonen | 6-4,6-3 |
| ITF M15 Vaasa | 2023/06/06 07:00 | Siim Troost v Oskari Eerola | 6-4,3-6,10-7 |
| ITF M15 Vaasa | 2023/06/05 07:00 | Siim Troost v Hermanni Tiainen | 6-4,6-2 |
| Challenger Poznan | 2023/06/19 09:00 | Rudolf Molleker v Kai Wehnelt | 6-4,6-4 |
| Challenger Poznan | 2023/06/18 08:30 | Kai Wehnelt v Kalin Ivanovski | 6-3,3-6,6-3 |
| ITF M15 Nyiregyhaza | 2023/06/07 08:00 | Peter Nad v Kai Wehnelt | 6-4,1-6,6-3 |
| ITF M25 Reggio Emilia | 2023/05/19 09:00 | Julian Ocleppo v Kai Wehnelt | 6-4,3-6,6-2 |
| ITF M25 Reggio Emilia | 2023/05/17 10:00 | Gian Marco Ortenzi v Kai Wehnelt | 0-6,2-6 |
| ITF M25 Reggio Emilia | 2023/05/15 16:30 | Kai Wehnelt v Federico Marchetti | 6-1,6-0 |
| ITF M25 Reggio Emilia | 2023/05/15 09:50 | Kai Wehnelt v Noah Perfetti | 6-3,3-6,10-6 |
| Challenger Francavilla | 2023/05/07 16:40 | Stefano Travaglia v Kai Wehnelt | 6-4,6-2 |