Stadium: Hard 20 Round: 62 Ground: Hardcourt outdoor
| 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 |
| ITF M15 Vero Beach | 2023/04/24 16:00 | Oren Vasser v Brett Winters | 6-2,2-6,10-8 |
| ITF M15 Heraklion | 2023/03/20 10:30 | Luca Fantini v Brett Winters | 6-3,6-3 |
| ITF M15 Frankfurt Am Main | 2023/08/07 08:00 | John H Lithen v Dennis Dragomirov | 6-2,6-4 |
| ITF M15 Novi Sad | 2023/07/31 07:00 | Nikola Mitrovic v Dennis Dragomirov | 6-4,4-6,11-9 |
| ITF M25 Telfs | 2023/07/17 13:45 | Timofey Stepanov v Dennis Dragomirov | 6-4,6-4 |
| ITF M25 Telfs | 2023/07/17 07:00 | Dennis Dragomirov v Davide Ferrarolli | 6-4,6-3 |
| ITF M25 Telfs | 2023/07/16 10:30 | Dennis Dragomirov v Francesco Schmitz | 6-1,6-2 |
| ITF M15 Sofia | 2023/07/05 09:30 | Dennis Dragomirov v Andreja Petrovic | 0-6,4-6 |
| ITF M15 Store | 2023/06/21 15:00 | Dennis Dragomirov v Dominik Kellovsky | 1-6,2-6 |
| ITF M15 Store | 2023/06/20 07:55 | Maurus Malgiaritta v Dennis Dragomirov | 2-6,6-3,7-10 |