Stadium: Court 7 Round: 26 Ground: Hardcourt outdoor
| ITF M25 Monastir | 2023/09/10 08:25 | Ilia Simakin v Ryan Seggerman | 5-7,4-6 |
| ITF M25 Monastir | 2023/09/09 08:30 | Abedallah Shelbayh v Ilia Simakin | 6-2,6-7,4-6 |
| ITF M25 Monastir | 2023/09/08 10:05 | Ilia Simakin v Thomas Braithwaite | 6-4,6-3 |
| ITF M25 Monastir | 2023/09/07 12:30 | Ilia Simakin v Maxim Zhukov | 6-4,4-6,6-1 |
| ITF M25 Monastir | 2023/09/05 10:35 | Ilia Simakin v Vladislav Ivanov | 6-4,6-3 |
| ITF M15 Monastir | 2023/09/02 08:30 | Ilia Simakin v Kris Van Wyk | 5-7,6-2,3-6 |
| ITF M15 Monastir | 2023/09/01 11:40 | Ilia Simakin v Ilya Snitari | 6-4,7-6 |
| ITF M15 Monastir | 2023/08/31 12:55 | Ilia Simakin v Leopold Zima | 6-1,6-4 |
| ITF M15 Ithaca | 2023/10/07 16:40 | Perry Gregg v Radu Mihai Papoe | 1-6,6-7 |
| ITF M15 Ithaca | 2023/10/06 15:00 | Perry Gregg v Ezekiel Clark | 6-3,6-1 |
| ITF M15 Ithaca | 2023/10/05 13:55 | Perry Gregg v Gabriel Evans | 6-2,7-6 |
| 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 |