Stadium: Court 2 Round: 26 Ground: Hardcourt outdoor
| ITF M25 Pensacola | 2023/05/17 13:50 | Keshav Chopra v Ryan Fishback | 4-6,6-3,4-6 |
| ITF M25 Pensacola | 2023/05/16 17:10 | Isaiah Strode v Keshav Chopra | 3-6,6-4,11-13 |
| ITF M25 Pensacola | 2023/05/15 18:00 | Timothy Phung v Keshav Chopra | 4-6,3-6 |
| UTR Pro Florida | 2023/05/13 16:30 | Keshav Chopra v Isaiah Strode | 6-3,4-6,6-7 |
| UTR Pro Florida | 2023/05/12 21:00 | Jerry Barton v Keshav Chopra | 3-6,3-6 |
| UTR Pro Florida | 2023/05/11 18:00 | Juan Pablo Cenoz v Keshav Chopra | 1-6,0-1 |
| UTR Pro Florida | 2023/05/10 17:00 | Dmitry Popko v Keshav Chopra | 6-4,6-2 |
| UTR Pro Florida | 2023/05/08 21:00 | Tom Pisane v Keshav Chopra | 1-6,1-6 |
| ITF M15 Krsko | 2023/05/17 08:00 | Pietro Pampanin v Timothy Gray | 6-4,2-6,10-7 |
| ITF M15 Krsko | 2023/05/15 08:00 | Timothy Gray v Benjamin Denis Alarcon | 3-6,6-2,10-3 |
| ITF M15 Monastir | 2023/05/01 12:30 | Linang Xiao v Timothy Gray | 6-1,6-0 |
| ITF M15 Monastir | 2023/04/23 08:30 | Timothy Gray v Oscar Lacides | 6-3,2-6,5-10 |
| ITF M15 Singapore | 2023/04/03 09:45 | Patrik Oplustil v Timothy Gray | 6-4,6-0 |
| ITF M15 Singapore | 2023/04/02 05:05 | Radu Ioan Popa v Timothy Gray | 3-6,2-6 |
| ITF M25 Swan Hill | 2023/02/28 02:25 | Omar Jasika v Timothy Gray | 6-1,6-2 |
| ITF M25 Swan Hill | 2023/02/22 00:00 | Timothy Gray v Aaron Addison | 1-6,7-5,6-7 |