Stadium: Court 6N Round: 54 Ground: Hardcourt outdoor
| ITF M25 Champaign | 2023/09/11 15:00 | Ryan Dickerson v Rollins, Pierce | 4-6,1-6 |
| ITF M25 Edwardsville | 2023/07/26 15:30 | Yuki Mochizuki v Rollins, Pierce | 6-2,6-1 |
| ITF M25 Edwardsville | 2023/07/25 13:30 | Rollins, Pierce v Bjorn Swenson | 4-6,6-3,10-7 |
| ITF M25 Champaign | 2023/07/19 20:40 | Rollins, Pierce v Cash Hanzlik | 2-6,2-6 |
| ITF M25 Champaign | 2023/07/18 17:15 | Rollins, Pierce v Nettles, Jibril | 7-5,6-3 |
| Dallas, Singles Main, M-ITF-USA-18A | 2023/07/11 14:50 | Rollins, Pierce v Franco Ribero | 4-6,6-7 |
| Tulsa, Singles Main, M-ITF-USA-16A | 2023/06/21 20:40 | Rollins, Pierce v James Trotter | 6-3,6-7,4-6 |
| ITF M25 Wichita | 2023/06/14 15:00 | Rollins, Pierce v Jaimee Floyd Angele | 4-6,4-6 |
| ITF M25 Champaign | 2023/09/11 15:00 | Sanchez Martinez, Benito v Gregg, Perry | 2-6,3-6 |
| ITF M25 Champaign | 2023/07/19 17:40 | Gregg, Perry v Ozan Baris | 5-7,4-6 |
| ITF M25 Champaign | 2023/07/18 14:55 | Gregg, Perry v Oliver Okonkwo | 3-6,6-2,10-7 |
| ITF M15 South Bend | 2023/06/22 16:55 | Gregg, Perry v James Tracy | 3-6,6-4,5-7 |
| ITF M15 South Bend | 2023/06/21 18:40 | Gregg, Perry v Fabien Salle | 6-4,6-4 |
| ITF M15 San Diego | 2023/06/13 17:30 | Warren Wood v Gregg, Perry | 6-3,7-5 |
| ITF M15 San Diego | 2023/06/05 17:00 | Galus, Piotr v Gregg, Perry | 5-7,7-6,10-6 |
| ITF M25 Malibu | 2023/01/03 21:20 | Rudy Quan v Gregg, Perry | 7-5,0-6,10-1 |