Stadium: Court 7 Round: 19 Ground: Hardcourt outdoor
| 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 |
| Challenger Matsuyama | 2023/11/11 05:15 | Taro Daniel v August Holmgren | 7-6,6-2 |
| Challenger Jokohama | 2023/11/19 06:50 | Kai Wehnelt v Yan Bai | 4-6,4-6 |
| Challenger Drummondville | 2023/11/12 20:20 | Kai Wehnelt v Nicaise Muamba | 4-6,6-4,6-7 |
| Challenger Calgary | 2023/11/06 17:00 | Kai Wehnelt v Patrick Brady | 1-6,6-7 |
| Challenger Sydney | 2023/10/30 02:10 | Rubin Statham v Kai Wehnelt | 6-4,7-6 |
| Challenger Sydney | 2023/10/29 02:20 | Sean Van Rensburg v Kai Wehnelt | 1-6,2-6 |
| Challenger Playford | 2023/10/23 23:30 | Kai Wehnelt v Yuta Shimizu | 4-6,4-6 |
| Challenger Playford | 2023/10/22 23:30 | Kai Wehnelt v Scott Jones | 6-3,6-7,7-6 |
| Challenger Playford | 2023/10/22 01:10 | Kai Wehnelt v Hayden Jones | 6-3,6-2 |