Stadium: Court 2 Round: 54 Ground: Clay
| ITF - M15 Cancun | 2022/07/10 14:00 | Brett Winters v Jaycer Lyeons | 6-7,1-6 |
| ITF - M25 Wesley Chapel | 2024/01/22 14:00 | Jaycer Lyeons v Pranav Kumar | 2-6,4-6 |
| ITF - M15 Santa Cruz | 2023/11/28 23:55 | Jaycer Lyeons v Leonardo Aboian | 1-6,2-6 |
| ITF - M15 Boca Raton | 2023/11/16 13:00 | Jaycer Lyeons v Kilian Feldbausch | 0-6,5-7 |
| UTR Pro Texas | 2023/08/26 13:00 | Jaycer Lyeons v Ethan Silva | 5-6 |
| UTR Pro Texas | 2023/08/25 23:00 | Jaycer Lyeons v Matthis Ross | 1-6,2-6 |
| UTR Pro Texas | 2023/08/24 00:30 | Jaycer Lyeons v Lathan Skrobarcek | 3-6,4-5 |
| UTR Pro Texas | 2023/08/22 13:00 | Jaycer Lyeons v JC Roddick | 0-6,2-6 |
| UTR Pro Texas | 2023/08/21 15:00 | Grant Lothringer v Jaycer Lyeons | 2-6,4-6 |
| ITF - M25 Ithaca | 2024/01/15 15:00 | James Aronson v Brett Winters | 7-6,6-2 |
| ITF - M25 Heraklion | 2023/11/27 08:00 | Brett Winters v Dennis Dragomirov | 5-7,1-6 |
| 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 |