Stadium: Court 1 Round: 54 Ground: Hardcourt indoor
| 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 |
| ITF M15 South Bend | 2023/06/20 15:00 | Brett Winters v Muzammil Murtaza | 4-6,4-6 |
| ITF M15 South Bend | 2023/06/19 14:00 | Cameron Muller v Brett Winters | 6-3,2-6,9-11 |
| ITF M15 Monastir | 2023/06/12 08:30 | Igor Kudriashov v Brett Winters | 6-1,6-1 |
| ITF M15 Monastir | 2023/06/04 08:30 | Brett Winters v Martin Borisiouk | 1-6,1-6 |
| ITF M15 Monastir | 2023/05/28 08:30 | Brett Winters v Jerome Iaconi | 6-7,7-6,6-10 |