Stadium: Court 3 Round: 26 Ground: Hardcourt outdoor
| ITF - Southaven M25 | 2023/08/09 18:30 | Gage Brymer v David Saye | 6-3,6-2 |
| ATP Washington | 2023/07/29 19:00 | Juncheng Shang v Gage Brymer | 6-3,6-2 |
| ITF - Edwardsville M25 | 2023/07/25 17:30 | Gage Brymer v Jaimee Floyd Angele | 4-6,1-6 |
| ATP Newport | 2023/07/17 15:00 | Gage Brymer v Yunseong Chung | 3-6,6-7 |
| ITF - Lakewood M15 | 2023/07/13 19:20 | Gage Brymer v Derek Pham | 5-7,3-6 |
| ITF - Lakewood M15 | 2023/07/12 21:15 | Gage Brymer v Isaiah Strode | 4-6,7-6,6-1 |
| ITF - Lakewood M15 | 2023/07/06 16:50 | Keegan Smith v Gage Brymer | 3-6,6-3,6-2 |
| ITF - Lakewood M15 | 2023/07/05 16:55 | Jaden Weekes v Gage Brymer | 6-7,5-7 |
| ITF - Southaven M25 | 2023/08/09 18:30 | Keshav Chopra v Conor Gannon | 1-6,6-2,6-4 |
| ITF - Southaven M25 | 2023/08/08 13:55 | Keshav Chopra v Alex Finkelstein | 6-1,6-2 |
| ITF - Decatur M25 | 2023/08/01 14:00 | Keshav Chopra v Logan Zapp | 4-6,4-6 |
| ITF - Decatur M25 | 2023/07/31 14:00 | Keshav Chopra v Piotr Lada | 6-0,6-1 |
| ATP Atlanta | 2023/07/22 18:30 | Arthur Cazaux v Keshav Chopra | 6-0,6-3 |
| ITF - Lakewood M15 | 2023/07/14 16:55 | Derek Pham v Keshav Chopra | 7-6,7-6 |
| ITF - Lakewood M15 | 2023/07/13 17:00 | Keshav Chopra v Ryan Seggerman | 6-3,2-6,6-4 |
| ITF - Lakewood M15 | 2023/07/12 19:25 | Emon Van Loben Sels v Keshav Chopra | 2-6,0-6 |