Stadium: Court 5 Round: 27 Ground: Hardcourt outdoor
| ITF M15 Colombo | 2022/07/22 04:00 | Singh, Digvijaypratap v Karan Singh | 6-2,5-7,6-2 |
| ITF M15 Ahmedabad | 2023/10/11 04:30 | Singh, Digvijaypratap v Shivank Bhatnagar | 6-7,6-2,6-3 |
| ITF M15 Ahmedabad | 2023/10/10 03:30 | Singh, Digvijaypratap v Ryotaro Matsumura | 6-2,6-4 |
| Alicante, Spain | 2023/10/01 10:10 | Daniel Cukierman v Singh, Digvijaypratap | 6-0,7-6 |
| Coupe Davis | 2023/09/17 11:30 | Singh, Digvijaypratap v Ahouda, Walid | 6-1,5-7,10-6 |
| ITF M25 Tainan | 2023/08/25 02:00 | Rishab Agarwal v Singh, Digvijaypratap | 2-6,6-3,6-4 |
| ITF M25 Tainan | 2023/08/24 03:50 | Lucio Carnevalle v Singh, Digvijaypratap | 2-6,2-6 |
| ITF M25 Tainan | 2023/08/22 01:55 | Ke Hau Hung v Singh, Digvijaypratap | 4-6,2-6 |
| ITF M25 Tainan | 2023/08/16 04:40 | Kazuki Nishiwaki v Singh, Digvijaypratap | 6-7,6-4,6-3 |
| ITF M15 Ahmedabad | 2023/10/11 04:30 | Luke Sorensen v Karan Singh | 0-6,1-6 |
| ITF M15 Ahmedabad | 2023/10/10 03:30 | Chirag Duhan v Karan Singh | 3-6,2-6 |
| ITF - M15 Monastir | 2023/09/27 08:30 | Phoenix Weir v Karan Singh | 7-5,7-6 |
| ITF - M15 Monastir | 2023/09/20 09:00 | Karan Singh v Keshav Chopra | 2-6,7-5,5-7 |
| ITF M25 Astana | 2023/08/02 05:55 | Alexander Zgirovsky v Karan Singh | 6-2,4-6,6-3 |
| ITF M25 Astana | 2023/08/01 04:00 | Karan Singh v Ibragimov, Daniel | 6-1,6-3 |
| Challenger Astana | 2023/07/25 04:00 | Karan Singh v Evgeny Karlovskiy | 6-7,2-6 |
| Challenger Astana | 2023/07/24 04:00 | Aliaksandr Liaonenka v Karan Singh | 3-6,6-7 |