Stadium: Hard 20 Round: 62 Ground: Hardcourt outdoor
| ITF M15 - Heraklion | 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 |
| ITF M15 - South Bend | 2023/06/20 15:00 | Brett Winters v Muzammil Murtaza | 4-6,4-6 |
| ITF M15 - Heraklion | 2023/11/20 10:00 | Dennis Dragomirov v Vasil Yehorov | 6-3,3-6,9-11 |
| ITF M15 - Heraklion | 2023/11/19 07:00 | Tomas Krcma v Dennis Dragomirov | 2-6,0-6 |
| UTR Pro - Olomouc | 2023/11/12 07:00 | Dennis Dragomirov v Jiri Cizek | 6-3,6-4 |
| UTR Pro - Olomouc | 2023/11/11 07:00 | Domagoj Biljesko v Dennis Dragomirov | 3-6,6-7 |
| UTR Pro - Olomouc | 2023/11/10 09:48 | Dennis Dragomirov v Oleg Prihodko | 2-6,3-6 |
| UTR Pro - Olomouc | 2023/11/09 10:00 | Dennis Dragomirov v Jakub Vrba | 6-3,7-5 |
| UTR Pro - Olomouc | 2023/11/08 07:00 | Christos Keisidis v Dennis Dragomirov | 5-7,3-6 |
| UTR Pro - Olomouc | 2023/11/07 11:52 | Gabor Mathe v Dennis Dragomirov | 7-6,2-6,4-6 |