Stadium: Court 5 Round: 27 Ground: Hardcourt outdoor
| 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 Pane | 7-5,6-3 |
| UTR - Pro Atlanta | 2023/04/13 12:30 | Edward Winter v Dhakshineswar Suresh | 5-7,1-6 |
| UTR - Pro Atlanta | 2023/04/12 18:00 | Samuel Reeve v Edward Winter | 0-6,2-6 |
| UTR - Pro Atlanta | 2023/04/11 22:15 | Santiago Villarruel v Edward Winter | 0-6,3-6 |
| ITF M25 - Calabasas | 2023/03/23 20:45 | Edward Winter v Alex Bolt | 3-6,6-7 |
| ITF - M15 Tacarigua | 2023/04/20 18:00 | Christopher Bulus v Kousuke Ogura | 2-6,4-6 |
| ITF - M15 Tacarigua | 2023/04/19 18:00 | Sebastien Byng v Kousuke Ogura | 1-6,0-6 |
| ITF - M15 De Los Tsachilas | 2023/04/11 18:00 | Tobias Franco v Kousuke Ogura | 4-6,6-4,7-5 |
| ITF - M15 De Los Tsachilas | 2023/04/07 18:00 | Kousuke Ogura v Andres Andrade | 6-4,6-7,2-6 |
| ITF - M15 De Los Tsachilas | 2023/04/06 14:00 | Kousuke Ogura v Nicolas Buitrago | 4-6,7-5,6-2 |
| ITF - M15 De Los Tsachilas | 2023/04/04 18:00 | Ezekiel Clark v Kousuke Ogura | 2-6,4-6 |
| ITF - M25 Montreal | 2023/03/16 14:00 | Kousuke Ogura v Henri Squire | 1-6,1-6 |
| ITF - M25 Montreal | 2023/03/15 14:00 | Kousuke Ogura v Aristotelis Thanos | 6-4,7-6 |