Stadium: Court 3 Round: 19 Ground: Hardcourt outdoor
| Challenger Yokohama | 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 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 Yokohama | 2023/11/19 01:00 | Naoki Tajima v Egor Gerasimov | 6-4,3-6,6-2 |
| ITF M25 Cairns | 2023/10/11 00:00 | Naoki Tajima v Jacob Brumm | 2-6,5-7 |
| ITF M25 Cairns | 2023/10/10 04:25 | Naoki Tajima v Thomas Patton | 7-6,6-0 |
| ITF M25 Cairns | 2023/10/10 00:00 | Naoki Tajima v Blake Bayldon | 6-2,7-6 |
| ITF M25 Cairns | 2023/10/05 00:00 | Naoki Tajima v Blake Ellis | 1-6,4-6 |
| ITF M25 Cairns | 2023/10/04 02:55 | Alexander Klintcharov v Naoki Tajima | 6-0,4-6,4-6 |
| ITF M25 Cairns | 2023/10/03 02:05 | Naoki Tajima v Lawrence Bataljin | 6-2,6-1 |
| ITF M25 Cairns | 2023/10/02 02:30 | Naoki Tajima v Hugo Joaquim Babakian | 6-0,6-1 |