Stadium: Court 5 Round: 25 Ground: Hardcourt outdoor
| Challenger Kobe | 2023/11/13 04:35 | Yusuke Takahashi v August Holmgren | 4-6,4-6 |
| Challenger Yokkaichi | 2023/11/27 01:00 | Yusuke Takahashi v Yuki Mochizuki | 6-2,3-6,7-6 |
| Challenger Yokkaichi | 2023/11/26 01:00 | Yusuke Takahashi v Arjun Kadhe | 6-0,6-3 |
| Challenger Jokohama | 2023/11/19 01:00 | Yusuke Takahashi v Naoki Nakagawa | 5-7,6-7 |
| Challenger Kobe | 2023/11/13 04:35 | Yusuke Takahashi v August Holmgren | 4-6,4-6 |
| 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 Yokkaichi | 2023/11/27 01:00 | August Holmgren v Kai Wehnelt | 6-2,6-4 |
| Challenger Jokohama | 2023/11/21 02:45 | August Holmgren v Giovanni Fonio | 4-6,1-6 |
| Challenger Jokohama | 2023/11/20 01:00 | August Holmgren v Naoki Tajima | 3-6,7-5,6-3 |
| Challenger Jokohama | 2023/11/19 02:55 | August Holmgren v James Trotter | 7-6,3-6,6-4 |
| Challenger Kobe | 2023/11/16 04:30 | August Holmgren v Luca Nardi | 3-6,6-3,5-7 |
| Challenger Kobe | 2023/11/14 02:45 | August Holmgren v Moez Echargui | 6-4,6-3 |
| Challenger Kobe | 2023/11/13 04:35 | Yusuke Takahashi v August Holmgren | 4-6,4-6 |
| Challenger Kobe | 2023/11/12 06:00 | August Holmgren v Omni Kumar | 6-2,6-3 |