Stadium: Court 1 Round: 25 Ground: Hardcourt outdoor
| ITF - M15 Tacarigua | 2023/04/26 14:00 | Edward Winter v Evan Bynoe | 2-6,2-6 |
| ITF - M15 Tacarigua | 2023/04/22 19:00 | Ezekiel Clark v Edward Winter | 6-1,6-3 |
| ITF - M15 Tacarigua | 2023/04/21 18:00 | Edward Winter v Kousuke Ogura | 6-2,6-4 |
| ITF - M15 Tacarigua | 2023/04/20 18:00 | Edward Winter v Finn Reynolds | 5-7,6-2,7-6 |
| UTR Pro Atlanta | 2023/04/16 14:30 | Chad Kissell v Edward Winter | 7-5,3-6,1-6 |
| UTR Pro Atlanta | 2023/04/15 20:33 | Edward Winter v Peter Bertran | 6-4,6-3 |
| UTR Pro Atlanta | 2023/04/15 01:00 | Edward Winter v Lautaro Lautaro Pane | 7-5,6-3 |
| UTR Pro Atlanta | 2023/04/13 12:30 | Edward Winter v Dhakshineswar Suresh | 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 Luis Humberto Lopez | 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 | Jett Middleton v Hudson Rivera | 1-6,6-7 |
| UTR Pro California | 2023/04/22 17:00 | Hudson Rivera v Lucas Gomez | 4-1 |
| UTR Pro California | 2023/04/21 17:00 | Lautaro Lautaro Pane v Hudson Rivera | 6-3,3-6,4-6 |