Stadium: Court 5 Round: 54 Ground: Hardcourt indoor
| 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 - M25 Champaign | 2023/07/18 14:55 | Perry Gregg v Oliver Okonkwo | 3-6,6-2,10-7 |
| ITF - M15 South Bend | 2023/06/22 16:55 | Perry Gregg v James Tracy | 3-6,6-4,5-7 |
| ITF - M15 Ithaca | 2023/10/02 16:30 | Brett Winters v Karol Malirz | 1-6,7-6,10-7 |
| ITF - M15 Pittsburgh | 2023/07/24 14:00 | Brett Winters v Nick Lagaev | 2-6,1-6 |
| ITF - M15 South Bend | 2023/06/20 15:00 | Brett Winters v Muzammil Murtaza | 4-6,4-6 |
| ITF - M15 South Bend | 2023/06/19 14:00 | Cameron Muller v Brett Winters | 6-3,2-6,9-11 |
| ITF - M15 Monastir | 2023/06/12 08:30 | Igor Kudriashov v Brett Winters | 6-1,6-1 |
| ITF - M15 Monastir | 2023/06/04 08:30 | Brett Winters v Martin Borisiouk | 1-6,1-6 |
| ITF - M15 Monastir | 2023/05/28 08:30 | Brett Winters v Jerome Iaconi | 6-7,7-6,6-10 |
| ITF - M15 Vero Beach | 2023/04/24 16:00 | Oren Vasser v Brett Winters | 6-2,2-6,10-8 |