| Davis Cup | 2021/06/22 08:00 | Kalin Ivanovski v Granit Bajraliu | 6-0,6-0 |
| ITF M15 Skopje | 2021/06/10 08:35 | Kalin Ivanovski v Obrad Markovski | 6-3,4-6,4-6 |
| ITF M15 Skopje | 2021/06/02 08:00 | Kalin Ivanovski v Alex Rybakov | 2-6,2-6 |
| ITF M15 Sibenik | 2021/05/19 12:30 | Rimpei Kawakami v Kalin Ivanovski | 6-0,6-2 |
| ITF M15 Sibenik | 2021/04/21 09:20 | Kalin Ivanovski v Lorenzo Bocchi | 7-6,4-6,6-7 |
| ITF M15 Monastir | 2021/01/12 09:00 | Yusuke Takahashi v Kalin Ivanovski | 6-2,6-4 |
| ITF M15 Heraklion | 2020/11/21 13:00 | Kalin Ivanovski v Adrian Andreev | 1-6,4-6 |
| ITF M15 Heraklion | 2020/11/19 09:35 | Lucas Gerch v Kalin Ivanovski | 6-7,6-7 |
| Davis Cup | 2021/06/22 08:00 | Damien Gelabert v Ilya Snitari | 1-6,2-6 |