Stadium: Court 2 Round: 54 Ground: Hardcourt outdoor
| ITF M25 Champaign | 2023/07/21 15:00 | Kenta Miyoshi v Naoki Nakagawa | 2-6,4-6 |
| ITF M25 Champaign | 2023/07/20 14:45 | Kenta Miyoshi v Cash Hanzlik | 6-3,3-6,6-2 |
| ITF M15 Santo Domingo | 2023/06/20 14:00 | Kenta Miyoshi v Ronald Hohmann | 6-3,1-6,2-6 |
| ITF M25 Daegu | 2023/06/07 03:00 | Kenta Miyoshi v Uisung Park | 5-7,3-6 |
| ITF M25 Daegu | 2023/06/05 06:10 | Kenta Miyoshi v Suk Ann | 6-4,6-3 |
| ITF M25 Daegu | 2023/06/04 01:00 | Kenta Miyoshi v Christian Heaney-Secord | 6-0,6-4 |
| ITF M15 Karuizawa | 2023/05/31 04:35 | Sora Fukuda v Kenta Miyoshi | 7-6,6-4 |
| ITF M15 Karuizawa | 2023/05/30 03:00 | Kenta Miyoshi v Luca Hesselmann | 6-1,6-2 |
| ITF M25 Champaign | 2023/07/18 14:55 | Perry Gregg v Oliver Okonkwo | 3-6,6-2,10-7 |
| ITF M15 South Bend | 2023/06/21 17:05 | Adhithya Ganesan v Oliver Okonkwo | 6-0,6-3 |
| ITF M15 South Bend | 2023/06/20 15:00 | John Bernard v Oliver Okonkwo | 2-6,4-6 |
| ITF M15 South Bend | 2023/06/19 14:00 | Oliver Okonkwo v Sean Daryabeigi | 3-6,6-3,13-11 |
| UTR Pro London | 2023/05/20 10:16 | Luka Petrovic v Oliver Okonkwo | 6-4,6-4 |
| UTR Pro London | 2023/05/19 07:00 | Oliver Okonkwo v Ben Hudson | 6-3,5-4 |
| UTR Pro London | 2023/05/17 08:30 | Oliver Okonkwo v Kabeer Kapasi | 6-2,6-1 |
| UTR Pro London | 2023/05/16 11:30 | Oliver Okonkwo v Andres Gabriel Ciurletti | 0-6,6-2,6-5 |