Stadium: Court 8 Round: 62 Ground: Hardcourt outdoor
| ITF M15 Edmond | 2023/01/24 16:00 | Brett Winters v Alexander Visser | 4-6,4-6 |
| ITF M15 Edmond | 2023/01/23 16:00 | Paul Spencer v Brett Winters | 4-6,6-3,9-11 |
| ITF M15 Ithaca | 2023/01/16 16:00 | Brett Winters v Andrei Duarte | 1-6,4-6 |
| ITF M15 Santo Domingo | 2022/11/21 14:00 | Paul Spencer v Brett Winters | 6-4,6-2 |
| ITF M15 Santo Domingo | 2022/11/20 13:00 | Enmanuel Munoz v Brett Winters | 4-6,3-6 |
| ITF M15 Sharm El Sheikh | 2022/10/24 10:30 | Finn Reynolds v Brett Winters | 6-0,6-3 |
| ITF M15 Sharm El Sheikh | 2022/10/23 08:00 | Brett Winters v Jasper Lai | 7-5,6-3 |
| ITF M15 Sharm El Sheikh | 2022/10/16 12:00 | Massimo Giunta v Brett Winters | 6-0,6-3 |
| ITF M25 Santo Domingo | 2023/02/12 13:00 | Manuel Paniagua v Zakhar Martsinkevich | 1-6,2-6 |
| ITF M15 Santo Domingo | 2022/11/27 14:00 | Manuel Paniagua v Joaquin Bianchi | 0-6,1-6 |