Stadium: Court 1 Round: 14 Ground: Clay
| 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 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 |
| Challenger San Benedetto | 2023/07/09 12:30 | Gabriele Piraino v Lorenzo Rottoli | 6-1,6-3 |
| Challenger Milan | 2023/07/02 10:40 | Salvatore Caruso v Lorenzo Rottoli | 6-0,6-4 |
| Challenger Modena | 2023/06/25 14:35 | Jules Marie v Lorenzo Rottoli | 7-5,6-3 |
| Challenger Parma | 2023/06/19 08:00 | Alex M Pujolras v Lorenzo Rottoli | 6-0,7-6 |
| Challenger Perugia | 2023/06/11 08:00 | Lorenzo Rottoli v Matteo Martineau | 2-6,6-7 |
| Challenger Vicenza | 2023/05/30 10:20 | Lorenzo Rottoli v Marco Trungelliti | 3-6,1-6 |
| ITF M25 Reggio Emilia | 2023/05/17 11:45 | Lorenzo Rottoli v Kyle Edmund | 0-6,6-7 |
| ITF M25 Santa Margherita | 2023/04/29 09:00 | Lorenzo Rottoli v Giovanni Oradini | 6-1,6-2 |