Stadium: Court 2 Round: 14 Ground: Hardcourt outdoor
| Challenger - Palmas del Mar | 2023/06/12 15:00 | Kaito Uesugi v Colin Sinclair | 1-6,6-7 |
| Challenger - Palmas del Mar | 2023/06/11 18:15 | Kaito Uesugi v Calum Puttergill | 6-3,6-1 |
| ITF - M25 Kashiwa | 2023/04/07 03:00 | Jeamoon Lee v Kaito Uesugi | 6-4,6-2 |
| ITF - M25 Kashiwa | 2023/04/06 03:40 | Kaito Uesugi v Issei Okamura | 6-1,6-4 |
| ITF - M25 Kashiwa | 2023/04/05 08:15 | Kaito Uesugi v Sora Fukuda | 2-6,6-2,6-2 |
| ITF - M25 Kashiwa | 2023/04/03 03:30 | Jeremy Jin v Kaito Uesugi | 4-6,1-6 |
| ITF - M25 Kashiwa | 2023/04/02 00:30 | Hayato Matsuoka v Kaito Uesugi | 7-5,3-6,9-11 |
| ITF - M25 Tsukuba | 2023/03/29 00:30 | Yu Hsiou Hsu v Kaito Uesugi | 7-6,6-4 |
| ITF - M15 Nakhon Si Thammarat | 2023/07/11 02:00 | Takuya Kumasaka v Karan Singh | 6-2,6-2 |
| ITF - M15 Nakhon Si Thammarat | 2023/07/05 04:05 | Karan Singh v Maximus Jones | 4-6,2-6 |
| ITF - M15 Jakarta | 2023/06/29 03:25 | Karan Singh v Thiemo De Bakker | 5-7,6-7 |
| ITF - M15 Jakarta | 2023/06/28 02:00 | Karan Singh v Justin Barki | 7-5,6-1 |
| ITF - M15 Jakarta | 2023/06/21 02:00 | Karan Singh v Nitin Kumar Sinha | 6-3,2-6,0-6 |
| ITF - M15 Tehran | 2023/06/15 06:30 | Grigoriy Lomakin v Karan Singh | 6-2,7-6 |
| ITF - M15 Tehran | 2023/06/14 08:15 | Luca Fantini v Karan Singh | 6-2,6-7,3-6 |
| ITF - M15 Tehran | 2023/06/10 09:30 | Lorenzo Bocchi v Karan Singh | 6-2,6-3 |