Stadium: Court 8 Round: 62 Ground: Hardcourt outdoor
| ITF M15 Monastir | 2023/06/19 08:30 | Ammar Faleh Alhogbani v Ryan A Dos Santos | 6-2,3-6,10-3 |
| ITF M15 Monastir | 2023/06/11 08:30 | Marcel Politowicz v Ryan A Dos Santos | 6-2,6-3 |
| ITF M15 Mogi das Cruzes | 2023/04/25 13:00 | Ryan A Dos Santos v Rafael Tosetto | 6-3,1-6,6-10 |
| ITF M15 Mogi das Cruzes | 2023/04/24 16:00 | Ryan A Dos Santos v Henrique S Gomes | 7-5,6-2 |
| ITF M15 Santo Domingo | 2023/04/10 14:00 | Mateo Barreiros Reyes v Ryan A Dos Santos | 6-2,6-3 |
| ITF M15 Santo Domingo | 2023/04/09 14:00 | Gustavo Teisen Pereira v Ryan A Dos Santos | 3-6,6-4,3-10 |
| ITF M15 Santo Domingo | 2023/04/02 14:00 | Ryan A Dos Santos v Patricio Alvarado | 6-1,6-7,10-4 |
| ITF M25 Mosquera | 2023/03/22 18:50 | Murkel Dellien v Ryan A Dos Santos | 6-2,6-3 |
| 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 |