Stadium: Court 3 Round: 14 Ground: Hardcourt outdoor
| 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 Hamburk | 2023/10/16 14:00 | Kalin Ivanovski v Jelle Sels | 2-6,4-6 |
| Challenger Bratislava | 2023/10/12 09:00 | Martin Damm v Kalin Ivanovski | 6-3,6-4 |
| Challenger Bratislava | 2023/10/10 10:40 | Kalin Ivanovski v Peter Gojowczyk | 7-6,6-2 |
| Challenger Bratislava | 2023/10/09 08:30 | Mate Valkusz v Kalin Ivanovski | 3-6,5-7 |
| Challenger Kobe | 2023/11/13 02:55 | Giovanni Fonio v Shinji Hazawa | 6-3,6-7,6-1 |
| ITF M15 Nakhon Si Thammarat | 2023/07/14 03:40 | Shinji Hazawa v Sidharth Rawat | 6-4,5-7,3-6 |
| ITF M15 Nakhon Si Thammarat | 2023/07/13 02:00 | Shinji Hazawa v Amir Milushev | 6-1,4-6,6-4 |
| ITF M15 Nakhon Si Thammarat | 2023/07/12 02:00 | Shinji Hazawa v Chase Ferguson | 6-7,6-1,6-2 |
| ITF M15 Nakhon Si Thammarat | 2023/07/06 06:25 | Shinji Hazawa v Ji Hoon Son | 6-3,3-6,6-7 |
| ITF M15 Nakhon Si Thammarat | 2023/07/04 02:00 | Shinji Hazawa v Sidharth Rawat | 6-3,6-1 |
| ITF M25 Nakhon Si Thammarat | 2023/06/16 02:00 | Shinji Hazawa v Hiroki Moriya | 4-6,5-7 |
| ITF M25 Nakhon Si Thammarat | 2023/06/15 03:20 | Shinji Hazawa v Pruchya Isarow | 6-3,6-4 |