Stadium: Court 5 Round: 25 Ground: Hardcourt outdoor
| Challenger - Yokohama | 2023/11/24 04:05 | Yosuke Watanuki v Giovanni Fonio | 3-6,6-2,6-1 |
| Challenger - Yokohama | 2023/11/23 05:15 | Giovanni Fonio v Leandro Riedi | 4-6,7-6,6-4 |
| Challenger - Yokohama | 2023/11/21 02:45 | August Holmgren v Giovanni Fonio | 4-6,1-6 |
| Challenger - Yokohama | 2023/11/20 03:30 | Giovanni Fonio v Colin Sinclair | 3-6,7-5,6-7 |
| Challenger - Yokohama | 2023/11/19 05:10 | Giovanni Fonio v Hiroki Moriya | 5-7,6-3,6-4 |
| Challenger - Kobe | 2023/11/14 05:00 | Giovanni Fonio v Shintaro Mochizuki | 6-4,2-6,3-6 |
| Challenger - Kobe | 2023/11/13 02:55 | Giovanni Fonio v Shinji Hazawa | 6-3,6-7,6-1 |
| Challenger - Kobe | 2023/11/12 05:25 | Giovanni Fonio v Hiroki Moriya | 7-5,6-2 |
| Challenger - Yokohama | 2023/11/23 01:30 | Kalin Ivanovski v Luca Nardi | 2-6,4-6 |
| Challenger - Yokohama | 2023/11/22 02:30 | Kalin Ivanovski v Zizou Bergs | 6-1,5-7,6-2 |
| Challenger - Yokohama | 2023/11/19 07:00 | Kalin Ivanovski v Shinji Hazawa | 3-6,6-4,7-5 |
| Challenger - Kobe | 2023/11/13 01:30 | Kalin Ivanovski v James Trotter | 5-7,7-6,6-4 |
| Challenger - Kobe | 2023/11/12 01:00 | Kalin Ivanovski v Ryuki Matsuda | 6-7,6-2,6-2 |
| Challenger - Bergamo | 2023/10/30 09:00 | Mikhail Kukushkin v Kalin Ivanovski | 3-6,7-6,6-4 |
| Challenger - Bergamo | 2023/10/29 09:00 | Alessio Balestrieri v Kalin Ivanovski | 2-6,1-6 |
| Challenger - Hamburg | 2023/10/16 14:00 | Kalin Ivanovski v Jelle Sels | 2-6,4-6 |