Stadium: Court 1 Round: 25 Ground: Hardcourt indoor
| Challenger Yokkaichi | 2023/11/27 04:45 | Giovanni Fonio v Kalin Ivanovski | 4-6,7-6,7-6 |
| 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 Braga | 2024/09/30 13:35 | Filip Jeff Planinsek v Francesco Passaro | 4-6,2-6 |
| Challenger Sibiu | 2024/09/17 12:35 | Stefano Travaglia v Filip Jeff Planinsek | 6-2,6-3 |
| Challenger Dobrich | 2024/09/10 14:50 | Filip Jeff Planinsek v David Jorda Sanchis | 6-3,3-6,6-7 |
| Challenger Como | 2024/08/26 15:40 | Francesco Passaro v Filip Jeff Planinsek | 6-2,4-6,6-4 |
| ITF M25 Maribor | 2024/08/21 10:00 | Filip Jeff Planinsek v Oleksandr Ovcharenko | 1-6,4-6 |
| ITF M25 Maribor | 2024/08/18 07:55 | Filip Jeff Planinsek v Mili Poljicak | 4-6,2-6 |
| ITF M25 Maribor | 2024/08/17 08:00 | Filip Jeff Planinsek v Bor Artnak | 3-6,6-3,7-6 |
| ITF M25 Maribor | 2024/08/16 10:00 | Filip Jeff Planinsek v David Poljak | 6-1,6-2 |