Stadium: Hard Court 2 Round: 62 Ground: Hardcourt outdoor
| ITF M25 Heraklion | 2023/11/12 07:00 | Benjamin Pietri v Brett Winters | 6-3,6-1 |
| ITF M15 Winston-Salem | 2023/11/06 17:00 | Mikel Anderson v Brett Winters | 6-0,6-4 |
| 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 M25 Heraklion | 2023/11/12 09:00 | Younes Lalami Laaroussi v Gabriel Matuszewski | 6-4,6-0 |
| ITF M25 Heraklion | 2023/11/05 11:00 | Gabriel Matuszewski v Mattia Ricci | 4-6,4-6 |
| ITF M25 Heraklion | 2023/10/30 09:30 | Guy Den Heijer v Gabriel Matuszewski | 6-1,6-4 |
| ITF M25 Heraklion | 2023/10/29 10:30 | Gianluca Carlini v Gabriel Matuszewski | 6-7,1-6 |
| ITF M15 Heraklion | 2023/10/22 08:30 | Gabriel Matuszewski v Stefan Cizelj-Zivkovic | 4-6,4-6 |
| ITF M15 Heraklion | 2023/10/17 06:30 | Ioannis Kountourakis v Gabriel Matuszewski | 6-3,6-0 |
| ITF M15 Heraklion | 2023/10/16 09:00 | Gianluca Carlini v Gabriel Matuszewski | 6-4,1-6,5-10 |
| UTR Pro Beograd | 2023/10/12 07:30 | Aleksa Mardjonovic v Gabriel Matuszewski | 0-3 |