Stadium: Court 2 Round: 54 Ground: Clay
| ITF M15 Naples | 2023/02/23 15:00 | Ryan Dickerson v Ozan Baris | 4-6,7-6,2-6 |
| ITF M15 Naples | 2023/02/22 17:35 | Gonzalo Bueno v Ryan Dickerson | 6-1,4-6,0-6 |
| ITF M15 Naples | 2023/02/21 15:30 | Juan Carlos Aguilar v Ryan Dickerson | 2-6,3-6 |
| ITF M15 Naples | 2023/02/20 17:00 | Joshua Nuyts v Ryan Dickerson | 2-6,2-6 |
| Weston, FL, Singles M-ITF-USA-05A | 2023/02/14 16:30 | Alejandro H Franco v Ryan Dickerson | 6-3,6-3 |
| Weston, FL, Singles M-ITF-USA-05A | 2023/02/13 16:30 | Ryan Dickerson v Warren Wood | 6-4,6-0 |
| ITF - M15 Palm Coast | 2023/02/07 15:00 | Isaiah Strode v Ryan Dickerson | 6-3,6-1 |
| ITF - M15 Palm Coast | 2023/02/06 15:00 | Rehman, Huzaifa A. v Ryan Dickerson | 1-6,1-6 |
| ITF M15 Naples | 2023/02/22 19:55 | Wojcik, Jakub v Nicolas Buitrago | 4-6,3-6 |
| ITF M15 Naples | 2023/02/21 15:30 | Wojcik, Jakub v Oren Vasser | 6-4,6-2 |
| ITF M15 Naples | 2023/02/20 17:00 | Wojcik, Jakub v van Emburgh, Jake | 6-2,6-1 |
| Weston, FL, Singles M-ITF-USA-05A | 2023/02/14 15:00 | Lucas Bouquet v Wojcik, Jakub | 6-4,7-5 |
| Weston, FL, Singles M-ITF-USA-05A | 2023/02/13 15:00 | Jonathan Irwanto v Wojcik, Jakub | 2-6,6-4,6-10 |
| ITF - M15 Palm Coast | 2023/02/07 15:00 | Wojcik, Jakub v Elijah Strode | 4-6,6-7 |
| ITF - M15 Palm Coast | 2023/02/06 15:00 | Wojcik, Jakub v Leo Vithoontien | 6-4,4-6,10-0 |
| ITF - M15 Antalya | 2023/01/24 10:25 | Wojcik, Jakub v Obrad Markovski | 1-6,1-6 |