Stadium: Center Court Round: 25 Ground: Hardcourt outdoor
| Challenger Granby | 2023/07/17 01:00 | Blake Ellis v Ajeet Rai | 5-7,6-4,7-5 |
| Challenger Busan | 2023/05/08 07:05 | Jason Jung v Ajeet Rai | 7-5,6-1 |
| Challenger Busan | 2023/05/08 02:00 | Jeamoon Lee v Ajeet Rai | 4-6,1-6 |
| Challenger Kwangdžu | 2023/04/30 01:30 | Ji Sung Nam v Ajeet Rai | 5-7,6-1,6-2 |
| Challenger Soul | 2023/04/23 02:00 | Shinji Hazawa v Ajeet Rai | 4-6,6-3,6-4 |
| Challenger Morelos | 2023/04/16 19:50 | Daniil Glinka v Ajeet Rai | 7-5,6-2 |
| Challenger - Leon | 2023/04/09 19:30 | Ajeet Rai v Nick Chappell | 4-6,7-5,2-6 |
| Challenger San Luis Potosi | 2023/04/03 20:45 | Nick Chappell v Ajeet Rai | 6-4,6-2 |
| ATP Bastad | 2023/07/17 08:00 | Timofey Skatov v Denis Yevseyev | 6-1,6-3 |
| Challenger Braunschweig | 2023/07/11 12:05 | Denis Yevseyev v Thiago Seyboth Wild | 6-4,4-6,1-6 |
| Challenger Braunschweig | 2023/07/10 11:50 | Yanaki Milev v Denis Yevseyev | 6-7,6-3,3-6 |
| Challenger Braunschweig | 2023/07/09 14:15 | Marc Majdandzic v Denis Yevseyev | 3-6,4-6 |
| Challenger Karlsruhe | 2023/07/04 15:30 | Denis Yevseyev v Thiago Seyboth Wild | 6-4,3-6,3-6 |
| Challenger Karlsruhe | 2023/07/03 10:35 | Denis Yevseyev v Sebastian Fanselow | 7-5,7-6 |
| Challenger Karlsruhe | 2023/07/02 13:50 | Denis Yevseyev v David Fix | 6-3,6-3 |
| Challenger Palmas del Mar | 2023/06/12 20:35 | Denis Yevseyev v Joao Lucas Reis da Silva | 7-5,4-6,5-7 |