Stadium: Court 1 Round: 27 Ground: Hardcourt outdoor
| ITF M25 Santo Domingo | 2023/06/29 13:30 | Darian King v Taha Baadi | 6-4,6-4 |
| ITF M25 Santo Domingo | 2023/06/28 16:50 | Osgar O'Hoisin v Darian King | 6-7,2-6 |
| ITF M25 Santo Domingo | 2023/06/27 14:45 | Darian King v Felipe Pinzon Moreno | 6-3,6-2 |
| ITF M25 Santo Domingo | 2023/06/26 15:00 | Darian King v Stephen Slocombe | 6-2,6-2 |
| ITF M15 Santo Domingo | 2023/06/24 13:30 | Liam Draxl v Darian King | 7-5,6-1 |
| ITF M15 Santo Domingo | 2023/06/23 13:30 | Darian King v Joshua Lapadat | 6-1,6-2 |
| ITF M15 Santo Domingo | 2023/06/22 13:30 | Darian King v Ronald Hohmann | 6-3,6-1 |
| ITF M15 Santo Domingo | 2023/06/21 13:30 | Yannik Rahman v Darian King | 2-6,4-6 |
| ITF M25 Santo Domingo | 2023/06/29 13:30 | Joshua Lapadat v Nick Chappell | 6-3,6-7,2-6 |
| ITF M25 Santo Domingo | 2023/06/28 18:50 | Brandon Perez v Nick Chappell | 4-6,1-6 |
| ITF M25 Tulsa | 2023/06/25 14:00 | Adam Walton v Nick Chappell | 6-1,6-3 |
| ITF M25 Tulsa | 2023/06/24 14:00 | Alfredo Perez v Nick Chappell | 5-7,3-6 |
| ITF M25 Tulsa | 2023/06/23 13:55 | Cannon Kingsley v Nick Chappell | 4-6,3-6 |
| ITF M25 Tulsa | 2023/06/22 17:45 | James Trotter v Nick Chappell | 4-6,5-7 |
| ITF M25 Tulsa | 2023/06/21 15:30 | Gabrielius Guzauskas v Nick Chappell | 6-7,4-6 |
| Challenger Palmas del Mar | 2023/06/13 19:30 | Rubin Statham v Nick Chappell | 6-1,6-7,7-5 |