Stadium: Court C Round: 25 Ground: Hardcourt indoor
| 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 |
| 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 01:30 | Yan Bai v Andrew Fenty | 6-4,3-6,4-6 |
| Challenger Kobe | 2023/11/12 04:35 | Arthur Weber v Yan Bai | 2-6,4-6 |
| Challenger Matsuyama | 2023/11/06 01:00 | Yan Bai v Hiroki Moriya | 6-1,3-6,1-6 |
| Challenger Matsuyama | 2023/11/05 01:00 | Yan Bai v Ryuki Matsuda | 6-2,6-4 |
| Challenger Shenzhen | 2023/10/20 04:05 | Bu Yunchaokete v Yan Bai | 6-3,6-2 |
| Challenger Shenzhen | 2023/10/19 04:00 | Yan Bai v Steven Diez | 3-6,6-1,6-4 |
| Challenger Shenzhen | 2023/10/16 08:35 | Arthur Weber v Yan Bai | 4-6,7-6,6-7 |
| Challenger Shenzhen | 2023/10/11 07:25 | Yan Bai v Pedro Cachin | 4-6,3-6 |