Stadium: TSITSIPAS COURT Round: 27 Ground: Hardcourt outdoor
| ITF M15 Heraklion | 2020/11/19 09:35 | Lucas Gerch v Kalin Ivanovski | 6-7,6-7 |
| ITF M15 Heraklion | 2020/11/18 12:30 | Kalin Ivanovski v Stefan Palosi | 7-5,6-2 |
| ITF M15 Heraklion | 2020/11/12 11:00 | Stuart Parker v Kalin Ivanovski | 6-2,6-0 |
| ITF M15 Heraklion | 2020/11/01 10:00 | Kalin Ivanovski v Nicholas David Ionel | 4-6,2-6 |
| Adriatic Tennis Series | 2020/06/16 14:30 | Carlos Gomez-Herrera v Kalin Ivanovski | 6-2,6-0 |
| ITF M15 Porec | 2020/03/09 09:00 | Pawel Juszczak v Kalin Ivanovski | 1-6,6-3,10-3 |
| ITF M15 Porec | 2020/03/08 09:10 | Obrad Markovski v Kalin Ivanovski | 3-6,1-6 |
| ITF M15 Antalya | 2019/11/03 07:00 | Kalin Ivanovski v Tomislav Jotovski | 2-6,4-6 |
| ITF M15 Heraklion | 2020/11/17 10:00 | Adrian Andreev v Natan Rodrigues | 6-0,6-1 |
| ATP Sofia | 2020/11/08 16:00 | John Millman v Adrian Andreev | 6-3,6-1 |
| ITF M15 Heraklion | 2020/10/27 07:00 | Evan Furness v Adrian Andreev | 6-3,6-3 |
| ITF M15 Heraklion | 2020/10/26 07:30 | Michalis Sakellaridis v Adrian Andreev | 1-6,3-6 |
| ITF M15 Heraklion | 2020/10/25 10:30 | Lodewijk Weststrate v Adrian Andreev | 3-6,2-6 |
| ITF M15 Melilla | 2020/09/26 09:30 | Holger Rune v Adrian Andreev | 7-6,6-1 |
| ITF M15 Melilla | 2020/09/25 12:40 | Eric Vanshelboim v Adrian Andreev | 6-7,2-6 |
| ITF M15 Melilla | 2020/09/24 11:10 | Francisco Andreu Garcia v Adrian Andreev | 4-6,1-6 |