Stadium: Court 7 Round: 62 Ground: Hardcourt outdoor
| 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 - M25 Heraklion | 2023/03/12 07:00 | Brett Winters v Valentin Guenther | 2-6,2-6 |
| ITF - M25 Montreal | 2023/03/06 21:35 | Brett Winters v Aurel Ciocanu | 1-6,2-6 |
| ITF - M25 Santo Domingo | 2023/02/20 14:00 | Mateo Barreiros Reyes v Brett Winters | 6-0,6-1 |
| ITF M25 Santo Domingo Qual | 2023/02/19 13:00 | Brett Winters v Manuel Paniagua | 2-6,1-6 |
| ITF - M15 Edmond | 2023/01/24 16:00 | Brett Winters v Alexander Visser | 4-6,4-6 |
| ITF - M15 Edmond | 2023/01/23 16:00 | Paul Spencer v Brett Winters | 4-6,6-3,9-11 |
| ITF - M15 Antalya | 2023/05/02 12:20 | Jerome Iaconi v Lior Goldenberg | 0-6,7-6,7-10 |
| ITF - M15 Antalya | 2023/05/01 09:35 | Nicolas Kobelt v Jerome Iaconi | 6-2,4-6,10-12 |
| ITF - M15 Antalya | 2023/04/30 07:00 | Jerome Iaconi v Lucas Nunez | 6-4,6-2 |
| ITF - M15 Antalya | 2023/04/24 09:20 | Jerome Iaconi v Loann Massard | 2-6,3-6 |
| ITF - M15 Antalya | 2023/04/23 07:00 | Alexandru Cristian Dumitru v Jerome Iaconi | 6-7,4-6 |
| ITF - M15 Monastir | 2022/09/26 08:00 | Jerome Iaconi v Maceo Simpson | 3-6,3-6 |
| ITF - M15 Monastir | 2022/09/25 09:00 | Kyle Gauci v Jerome Iaconi | 3-6,6-7 |
| ITF - M15 Monastir | 2022/09/19 08:00 | Taiyo Yamanaka v Jerome Iaconi | 6-2,6-2 |