Stadion: Court 5 Round: 19 Ground: Hardcourt outdoor
| 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 - M25 - Tsukuba | 2023/03/27 07:35 | Kaito Uesugi v Shohei Chikami | 5-7,6-1,10-5 |
| Challenger - Palmas del Mar | 2023/06/11 18:40 | Henrik Wiersholm v Colin Sinclair | 2-6,1-6 |
| ITF - M15 - Rancho Santa Fe | 2023/06/04 20:05 | Colin Sinclair v Jaimee Floyd Angele | 6-3,6-2 |
| ITF - M15 - Rancho Santa Fe | 2023/06/03 16:55 | Noah Schachter v Colin Sinclair | 3-6,5-7 |
| ITF - M15 - Rancho Santa Fe | 2023/06/02 20:00 | Colin Sinclair v Juan Carlos Aguilar | 6-3,6-0 |
| ITF - M15 - Rancho Santa Fe | 2023/06/01 21:45 | Colin Sinclair v Gianni Ross | 6-3,2-6,7-6 |
| ITF - M15 - Rancho Santa Fe | 2023/05/31 19:20 | Colin Sinclair v Ethan Schiffman | 7-6,6-2 |
| ITF - M25 - Pensacola | 2023/05/18 15:30 | Blu Baker v Colin Sinclair | 7-6,6-1 |
| ITF - M25 - Pensacola | 2023/05/17 13:50 | Chad Kissell v Colin Sinclair | 3-6,3-6 |