Stadium: Court 2N Round: 54 Ground: Hardcourt outdoor
| ITF M15 - Pittsburgh | 2023/07/27 17:15 | Ryan Dickerson v Darian King | 7-5,1-6,1-6 |
| ITF M15 - Pittsburgh | 2023/07/26 17:40 | Tyler Stice v Ryan Dickerson | 6-2,4-6,1-6 |
| ITF M15 - Pittsburgh | 2023/07/25 14:00 | Ryan Dickerson v Semen Pankin | 6-1,6-1 |
| ITF M15 - Pittsburgh | 2023/07/24 14:00 | Ryan Dickerson v Nicholas Heng | 6-3,6-3 |
| ITF M15 - Rochester | 2023/07/19 14:30 | Ryan Dickerson v Tyler Stice | 6-7,1-6 |
| ITF M15 - Huntsville | 2023/05/24 21:55 | Ryan Dickerson v Tristan McCormick | 4-6,3-6 |
| ITF M15 - Huntsville | 2023/05/23 17:00 | Ryan Dickerson v Hank Trondson | 6-2,6-0 |
| ITF M25 - Pensacola | 2023/05/17 17:40 | Bruno Kuzuhara v Ryan Dickerson | 4-6,7-5,6-5 |
| ITF M25 - Edwardsville | 2023/07/26 15:30 | Yuki Mochizuki v Pierce Rollins | 6-2,6-1 |
| ITF M25 - Edwardsville | 2023/07/25 13:30 | Pierce Rollins v Bjorn Swenson | 4-6,6-3,10-7 |
| ITF M25 - Champaign | 2023/07/19 20:40 | Pierce Rollins v Cash Hanzlik | 2-6,2-6 |
| ITF M25 - Champaign | 2023/07/18 17:15 | Pierce Rollins v Jibril Nettles | 7-5,6-3 |
| ITF M25 - Dallas | 2023/07/11 14:50 | Pierce Rollins v Franco Ribero | 4-6,6-7 |
| ITF M25 - Tulsa | 2023/06/21 20:40 | Pierce Rollins v James Trotter | 6-3,6-7,4-6 |
| ITF M25 - Wichita | 2023/06/14 15:00 | Pierce Rollins v Jaimee Floyd Angele | 4-6,4-6 |
| ITF M25 - Wichita | 2023/06/13 16:55 | Matthew Summers v Pierce Rollins | 6-4,5-7,6-10 |