Stadium: Court 1 Round: 54 Ground: Hardcourt indoor
| ITF M15 Morelia | 2023/10/17 18:30 | James Aronson v Juan Arturo Espanol Moreno | 4-6,2-6 |
| ITF M25 Heraklion | 2023/11/27 08:00 | Brett Winters v Dennis Dragomirov | 5-7,1-6 |
| ITF M15 Heráklion | 2023/11/20 07:00 | Brett Winters v Gabriel Matuszewski | 7-5,2-6,5-10 |
| ITF M25 Heraklion | 2023/11/12 07:00 | Benjamin Pietri v Brett Winters | 6-3,6-1 |
| ITF M25 Saint-Augustin | 2023/10/24 15:50 | Kuang Qing Xu v Brett Winters | 6-2,6-4 |
| ITF M25 Saint-Augustin | 2023/10/23 18:30 | Piotr Lada v Brett Winters | 0-6,1-6 |
| ITF M15 Ithaca | 2023/10/03 14:00 | Perry Gregg v Brett Winters | 6-3,6-0 |
| ITF M15 Ithaca | 2023/10/02 16:30 | Brett Winters v Karol Malirz | 1-6,7-6,10-7 |
| ITF M15 Pittsburgh | 2023/07/24 14:00 | Brett Winters v Nick Lagaev | 2-6,1-6 |