Stadium: Court 1 Round: 25 Ground: Hardcourt outdoor
| ITF M15 Tacarigua | 2023/04/26 14:00 | Winter, Edward v Bynoe, Evan | 2-6,2-6 |
| ITF M15 Tacarigua | 2023/04/22 19:00 | 클라크, 에제키엘 v Winter, Edward | 6-1,6-3 |
| ITF M15 Tacarigua | 2023/04/21 18:00 | Winter, Edward v 오구라, 코스케 | 6-2,6-4 |
| ITF M15 Tacarigua | 2023/04/20 18:00 | Winter, Edward v Reynolds, Finn | 5-7,6-2,7-6 |
| UTR Pro Atlanta | 2023/04/16 14:30 | Kissell, Chad v Winter, Edward | 7-5,3-6,1-6 |
| UTR Pro Atlanta | 2023/04/15 20:33 | Winter, Edward v 벨트란, 페터 | 6-4,6-3 |
| UTR Pro Atlanta | 2023/04/15 01:00 | Winter, Edward v Pane, Lautaro | 7-5,6-3 |
| UTR Pro Atlanta | 2023/04/13 12:30 | Winter, Edward v Suresh, Dhakshineswar | 5-7,1-6 |
| UTR Pro California | 2023/05/14 17:00 | Hudson Rivera v Emin Torlic | 6-2,7-6 |
| UTR Pro California | 2023/05/13 23:00 | Hudson Rivera v ZhengQing Ji | 7-6,5-7,6-3 |
| UTR Pro California | 2023/05/12 18:30 | Hudson Rivera v 로페즈, 루이스 훔버토 | 6-3,3-6,4-6 |
| UTR Pro California | 2023/05/10 18:30 | Hudson Rivera v Tobias Luo | 6-3,5-2 |
| UTR Pro California | 2023/05/09 17:00 | Hudson Rivera v Krish Arora | 6-4,5-4 |
| UTR Pro California | 2023/05/08 18:30 | 미들턴, 제트 v Hudson Rivera | 1-6,6-7 |
| UTR Pro California | 2023/04/22 17:00 | Hudson Rivera v 고메즈, 루카스 | 4-1 |
| UTR Pro California | 2023/04/21 17:00 | Pane, Lautaro v Hudson Rivera | 6-3,3-6,4-6 |