Stadium: Court 2 Round: 62 Ground: Clay
| ITF M15 Villa Maria | 2023/10/29 13:00 | Hess, Sean v Ayrton Andres Rodriguez | 6-3,6-0 |
| ITF M25 Lajeado | 2023/10/11 12:00 | 레이트, 윌슨 v Hess, Sean | 6-0,6-0 |
| ITF M25 Lajeado | 2023/10/10 14:50 | Hess, Sean v Nahuel Fernandez | 6-4,6-1 |
| ITF M25 Lajeado | 2023/10/09 16:00 | Hess, Sean v Tumasonis, Gabriel Pascotto | 6-3,6-2 |
| ITF M25 Mendoza | 2023/10/06 15:55 | 데스코트, 마티아스 프란코 v Hess, Sean | 4-6,6-3,7-6 |
| ITF M25 Mendoza | 2023/10/05 18:30 | Hess, Sean v Lautaro Midon | 2-6,6-4,6-0 |
| ITF M25 Mendoza | 2023/10/04 16:10 | 주카스, 마티아스 v Hess, Sean | 6-2,3-6,1-6 |
| ITF M25 Mendoza | 2023/10/03 12:00 | Hess, Sean v Mateo Matulovich | 6-0,6-4 |
| ITF M15 Villa Maria | 2023/10/29 13:00 | Mateo Branc v Ryan A Dos Santos | 1-6,4-6 |
| Challenger Curitiba | 2023/10/22 17:40 | 데 카르발호 카르도소 알베스, 마테우스 v Ryan A Dos Santos | 6-2,6-3 |
| ITF M25 Lajeado | 2023/10/10 12:55 | 피니, 프란시스코 v Ryan A Dos Santos | 6-2,5-7,15-13 |
| ITF M25 Lajeado | 2023/10/09 16:00 | Glauco Pinheiro Da Cruz Junior v Ryan A Dos Santos | 1-6,3-6 |
| ITF M25 Punta del Este | 2023/09/18 13:00 | Ryan A Dos Santos v Manuel Mouilleron Salvo | 1-6,4-6 |
| Sao Paulo, Singles M-ITF-BRA-06A | 2023/08/22 17:20 | Ryan A Dos Santos v William Norton | 1-6,2-6 |
| Sao Paulo, Singles M-ITF-BRA-06A | 2023/08/21 14:00 | 레알, 비톨 v Ryan A Dos Santos | 2-6,6-7 |
| ITF M15 Belem | 2023/08/14 13:00 | Valentin Basel v Ryan A Dos Santos | 6-3,6-2 |