Stadium: Court 2 Round: 54 Ground: Hardcourt outdoor
| ITF Indonesia F2 | 2018/08/01 03:40 | Shohei Chikami v Kaito Uesugi | 1-6,2-6 |
| ITF - Tsukuba M25 | 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 |
| Challenger Noumea | 2023/01/02 00:00 | Calum Puttergill v Kaito Uesugi | 6-1,2-6,7-5 |
| Challenger Noumea | 2023/01/01 00:00 | Gillian Osmont v Kaito Uesugi | 3-6,1-6 |
| Challenger Busan | 2022/10/16 04:10 | Shinji Hazawa v Kaito Uesugi | 6-2,6-1 |
| ITF - Kashiwa M25 | 2022/09/27 00:55 | Koki Matsuda v Kaito Uesugi | 3-6,6-4,6-0 |
| Challenger Rome GA | 2022/07/10 22:55 | Kaito Uesugi v Mukund Sasikumar | 6-4,6-7,1-6 |
| ITF - Tsukuba M25 | 2023/03/27 00:30 | Krittin Koaykul v Shohei Chikami | 1-6,3-6 |
| ITF - Aktobe M15 | 2023/03/09 04:55 | Shohei Chikami v Alexandr Binda | 3-6,3-6 |
| ITF - Aktobe M15 | 2023/03/08 09:50 | Shohei Chikami v Alexander Zgirovsky | 6-4,6-0 |
| ITF - Aktobe M15 | 2023/03/01 05:00 | Evgeny Philippov v Shohei Chikami | 6-1,7-6 |
| ITF - Aktobe M15 | 2023/02/28 06:35 | Shohei Chikami v Karlo Cubelic | 7-6,6-3 |
| ITF - Aktobe M15 | 2023/02/27 07:45 | Shohei Chikami v Vitaliy Zatsepin | 6-1,4-6,10-5 |
| ITF - Monastir M15 | 2023/02/03 09:00 | Shohei Chikami v Luca Giacomini | 6-4,2-6,3-6 |
| ITF - Monastir M15 | 2023/02/02 09:00 | Shohei Chikami v Taisei Ichikawa | 6-0,6-0 |