Stadium: Court 3 Round: 26 Ground: Hardcourt outdoor
| ITF Japan F2 | 2018/03/15 02:35 | Issei Okamura v Kaito Uesugi | 4-6,5-7 |
| ITF Japan F4 | 2017/03/28 03:00 | Kaito Uesugi v Issei Okamura | 6-3,6-3 |
| 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 |
| ITF M25 Tsukuba | 2023/03/27 00:30 | Kaito Uesugi v Takeru Yuzuki | 3-6,6-4,10-8 |
| Challenger Manama | 2023/02/13 08:00 | Kaito Uesugi v Yanki Erel | 4-6,3-6 |
| Challenger Manama | 2023/02/12 08:00 | Roman Jebavy v Kaito Uesugi | 4-6,1-6 |
| ITF M25 Kashiwa | 2023/04/05 05:35 | Issei Okamura v Sho Shimabukuro | 7-6,0-6,7-6 |
| ITF M25 Kashiwa | 2023/04/03 01:00 | Koki Matsuda v Issei Okamura | 1-6,2-6 |
| ITF M25 Kashiwa | 2023/04/02 00:30 | Taketo Takamisawa v Issei Okamura | 1-6,2-6 |
| ITF M25 Tsukuba | 2023/03/27 05:00 | Ryotaro Taguchi v Issei Okamura | 7-5,6-2 |
| ITF M25 Tsukuba | 2023/03/27 00:30 | Seiya Nakanishi v Issei Okamura | 2-6,4-6 |
| ITF M15 Aktobe | 2023/03/06 09:40 | Issei Okamura v Mykhailo Mossur | 4-6,6-3,5-10 |
| ITF M15 Aktobe | 2023/02/28 07:30 | Issei Okamura v Max Batyutenko | 6-7,6-4,7-10 |
| ITF M15 Aktobe | 2023/02/27 10:55 | Issei Okamura v Alexander Orlov | 6-2,7-6 |