Stadium: Court 5 Round: 25 Ground: Hardcourt outdoor
| Challenger Alicante | 2023/10/01 10:10 | Daniel Cukierman v Digvijay Pratap Singh | 6-0,7-6 |
| Davis Cup | 2023/09/17 11:30 | Digvijay Pratap Singh v Walid Ahouda | 6-1,5-7,10-6 |
| ITF M25 Tainan | 2023/08/25 02:00 | Rishab Agarwal v Digvijay Pratap Singh | 2-6,6-3,6-4 |
| ITF M25 Tainan | 2023/08/24 03:50 | Lucio Carnevalle v Digvijay Pratap Singh | 2-6,2-6 |
| ITF M25 Tainan | 2023/08/22 01:55 | Ke Hau Hung v Digvijay Pratap Singh | 4-6,2-6 |
| ITF M25 Tainan | 2023/08/16 04:40 | Kazuki Nishiwaki v Digvijay Pratap Singh | 6-7,6-4,6-3 |
| Challenger Astana | 2023/07/24 10:20 | Digvijay Pratap Singh v Renta Tokuda | 3-6,4-6 |
| ITF M15 Nakhon Si Thammarat | 2023/07/13 04:45 | Digvijay Pratap Singh v Pawit Sornlaksup | 2-6,2-6 |
| ITF M25 Takasaki | 2023/09/21 02:00 | Ryotaro Matsumura v Sora Fukuda | 1-6,1-6 |
| ITF M25 Takasaki | 2023/09/20 01:00 | Ryotaro Matsumura v Toru Horie | 6-0,5-7,7-6 |
| ITF M25 Takasaki | 2023/09/18 00:50 | Ryotaro Matsumura v Natsuki Yamamoto | 6-2,6-1 |
| ITF M25 Takasaki | 2023/09/17 01:00 | Ryotaro Matsumura v Seiya Nakanishi | 6-2,6-4 |
| ITF M25 Sapporo | 2023/09/10 03:00 | Ryotaro Matsumura v Yuta Tomida | 6-3,6-7,9-11 |
| ITF M25 Sapporo | 2023/09/08 01:00 | Sora Fukuda v Ryotaro Matsumura | 4-6,6-3,6-4 |
| ITF M25 Sapporo | 2023/09/07 03:00 | Ryotaro Matsumura v Tatsuma Ito | 7-6,6-4 |
| UTR Pro Noda | 2023/08/26 04:45 | Naoya Honda v Ryotaro Matsumura | 6-2,6-1 |