Stadium: Court E-1 Round: 27 Ground: Clay
| UTR Pro Florida | 2023/06/25 13:00 | Dimitri Badra v Henrik Wiersholm | 7-6,2-6,3-6 |
| UTR Pro Florida | 2023/06/24 14:30 | Ritesh Patil v Henrik Wiersholm | 3-6,1-6 |
| UTR Pro Florida | 2023/06/23 14:30 | Henrik Wiersholm v Matthew Rankin | 6-3,6-3 |
| UTR Pro Florida | 2023/06/21 13:30 | Henrik Wiersholm v Corey Craig | 6-3,4-6,0-6 |
| UTR Pro Florida | 2023/06/20 16:11 | Henrik Wiersholm v Azariah Rusher | 6-4,6-1 |
| UTR Pro Florida | 2023/06/19 18:00 | Evan Wen v Henrik Wiersholm | 1-6,0-5 |
| Challenger Palmas del Mar | 2023/06/11 18:40 | Henrik Wiersholm v Colin Sinclair | 2-6,1-6 |
| UTR Pro Florida | 2023/05/06 19:11 | Lachlan Brain v Henrik Wiersholm | 3-6,6-3,5-1 |
| ITF M25 Santo Domingo | 2023/06/30 13:30 | Darian King v Nick Chappell | 2-6,2-6 |
| 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 |