Stadium: Court B Round: 19 Ground: Hardcourt indoor
| Challenger Matsuyama | 2023/11/06 01:00 | Naoki Nakagawa v Yusuke Takahashi | 6-3,6-2 |
| Challenger Matsuyama | 2023/11/05 04:10 | Yusuke Kusuhara v Yusuke Takahashi | 2-6,2-6 |
| Challenger Sydney | 2023/10/31 02:20 | Dane Sweeny v Yusuke Takahashi | 4-6,6-3,7-6 |
| Challenger Sydney | 2023/10/29 23:00 | Yusuke Takahashi v Ji Sung Nam | 3-6,1-6 |
| Challenger Sydney | 2023/10/28 23:00 | Yusuke Takahashi v Bang Shuo Yin | 6-2,6-3 |
| Challenger Playford | 2023/10/24 02:55 | Thanasi Kokkinakis v Yusuke Takahashi | 6-7,6-3,6-2 |
| Challenger Playford | 2023/10/22 23:30 | Yusuke Takahashi v Ryan Seggerman | 6-3,6-2 |
| Challenger Playford | 2023/10/21 23:30 | Yusuke Takahashi v Shohei Chikami | 6-7,6-3,6-2 |
| Challenger Kobe | 2023/11/12 06:00 | August Holmgren v Omni Kumar | 6-2,6-3 |
| Challenger Matsuyama | 2023/11/11 05:15 | Taro Daniel v August Holmgren | 7-6,6-2 |
| Challenger Matsuyama | 2023/11/11 01:00 | Duje Ajdukovic v August Holmgren | 5-7,6-3,6-7 |
| Challenger Matsuyama | 2023/11/09 03:10 | Yasutaka Uchiyama v August Holmgren | 6-7,6-7 |
| Challenger Matsuyama | 2023/11/08 01:00 | August Holmgren v Marc Polmans | 6-0,6-4 |
| Challenger Matsuyama | 2023/11/06 01:00 | Egor Gerasimov v August Holmgren | 4-6,6-7 |
| ITF M25 Harlingen | 2023/10/29 17:00 | Raphael Perot v August Holmgren | 3-6,7-6,1-6 |
| ITF M25 Harlingen | 2023/10/28 16:00 | Kyle Kang v August Holmgren | 5-7,4-6 |