Stadium: Court 2 Round: 26 Ground: Hardcourt outdoor
| ITF M15 Monastir | 2023/09/20 09:00 | Karan Singh v Keshav Chopra | 2-6,7-5,5-7 |
| ITF M15 Monastir | 2023/09/18 12:30 | Keshav Chopra v Gianluca Carlini | 4-6,6-1,10-5 |
| ITF M15 Monastir | 2023/09/18 08:00 | Keshav Chopra v Riccardo Campagnola | 6-0,6-1 |
| ITF M15 Monastir | 2023/09/17 12:00 | Keshav Chopra v Matteo Fondriest | 6-1,7-6 |
| ITF M25 Monastir | 2023/09/13 08:30 | Keshav Chopra v Robin Bertrand | 3-6,3-6 |
| ITF M25 Monastir | 2023/09/05 10:30 | Devin Badenhorst v Keshav Chopra | 6-2,6-2 |
| UTR Pro California | 2023/08/27 19:16 | Hudson Rivera v Keshav Chopra | 2-6,2-5 |
| UTR Pro California | 2023/08/24 19:30 | Keshav Chopra v Noah Berry | 6-2,6-7,7-5 |
| ITF M15 Monastir | 2023/09/11 09:45 | Valentin Lapalu v Timothy Gray | 6-2,7-5 |
| ITF M15 Monastir | 2023/09/10 09:30 | Milosz Sroka v Timothy Gray | 4-6,5-7 |
| ITF M25 Monastir | 2023/09/05 10:00 | Abedallah Shelbayh v Timothy Gray | 6-2,6-2 |
| ITF M15 Monastir | 2023/08/30 11:20 | Alexandros Skorilas v Timothy Gray | 6-3,3-6,6-3 |
| ITF M15 Monastir | 2023/08/28 14:00 | Aaron Gil Garcia v Timothy Gray | 3-6,6-7 |
| ITF M15 Monastir | 2023/08/27 08:00 | Ahmed Mouhan v Timothy Gray | 2-6,1-6 |
| ITF M25 Herzlia | 2023/08/07 09:30 | Alon Elia v Timothy Gray | 6-7,1-6 |
| ITF M25 Herzlia | 2023/08/06 06:30 | Niv Zuckerman v Timothy Gray | 1-6,4-6 |