Stadium: Court 7 Round: 62 Ground: Hardcourt outdoor
| ITF M15 Monastir | 2023/06/25 08:30 | Nicolas Philibert v James Connel | 3-6,4-6 |
| ITF M15 Monastir | 2023/06/22 09:50 | Antoine Ghibaudo v James Connel | 6-3,6-3 |
| ITF M15 Monastir | 2023/06/21 09:50 | James Connel v Samir Hamza Reguig | 6-3,7-6 |
| ITF M15 Monastir | 2023/06/19 14:00 | James Connel v Linghao Zhang | 6-2,6-1 |
| 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 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 |