Stadium: Court 4 Round: 26 Ground: Hardcourt indoor
| ITF M15 Ithaca | 2023/10/04 14:00 | Shunsuke Mitsui v Perry Gregg | 3-6,6-7 |
| 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 | Perry Gregg v Bradley Paliska | 7-6,6-2 |
| ITF M15 Champaign | 2023/09/14 17:00 | Liam Draxl v Perry Gregg | 6-2,6-7,7-5 |
| ITF M15 Champaign | 2023/09/13 15:00 | Perry Gregg v Joshua Lapadat | 6-4,4-6,7-6 |
| ITF M25 Champaign | 2023/09/12 16:40 | Pierce Rollins v Perry Gregg | 3-6,6-7 |
| ITF M25 Champaign | 2023/09/11 15:00 | Benito Sanchez Martinez v Perry Gregg | 2-6,3-6 |
| ITF M25 Champaign | 2023/07/19 17:40 | Perry Gregg v Ozan Baris | 5-7,4-6 |
| ITF M15 Ithaca | 2023/10/04 14:00 | Ryan Dickerson v Gabriel Evans | 2-6,4-6 |
| ITF M15 Ithaca | 2023/10/03 14:00 | Gabriel Evans v Jibril Nettles | 6-4,6-4 |
| ITF M15 Albuquerque | 2023/09/26 14:00 | Axel Nefve v Gabriel Evans | 6-4,6-2 |
| ITF M15 Albuquerque | 2023/09/25 14:00 | Avery Tallakson v Gabriel Evans | 4-6,3-6 |
| ITF M25 Champaign | 2023/09/12 16:40 | Gabriel Evans v Maxwell McKennon | 6-7,6-2,6-10 |
| ITF M25 Champaign | 2023/09/11 20:30 | Gabriel Evans v Tyler Bowers | 6-3,6-2 |
| UTR Pro Fort Worth | 2023/09/10 00:47 | Jerry Barton v Gabriel Evans | 6-3,3-6,6-3 |
| UTR Pro Fort Worth | 2023/09/08 00:00 | Gabriel Evans v Pedro Vives Marcos | 1-6,6-3,7-6 |