| Challenger - Yokkaichi | 11/27 04:45 | 25 | [285] Giovanni Fonio v Kalin Ivanovski [305] | 4-6,7-6,7-6 | |
| Challenger - Yokohama | 11/23 01:30 | 26 | [323] Kalin Ivanovski v Luca Nardi [118] | 2-6,4-6 | |
| Challenger - Yokohama | 11/22 02:30 | 25 | [323] Kalin Ivanovski v Zizou Bergs [152] | 6-1,5-7,6-2 | |
| Challenger - Yokohama | 11/20 03:15 | 19 | [330] Kalin Ivanovski v Yan Bai [393] | Retired | |
| Challenger - Yokohama | 11/19 07:00 | 14 | [330] Kalin Ivanovski v Shinji Hazawa [311] | 3-6,6-4,7-5 | |
| Challenger - Kobe | 11/14 05:25 | 25 | [330] Kalin Ivanovski v Yan Bai [393] | Retired | |
| Challenger - Kobe | 11/13 01:30 | 19 | [326] Kalin Ivanovski v James Trotter [387] | 5-7,7-6,6-4 | |
| Challenger - Kobe | 11/12 01:00 | 14 | [326] Kalin Ivanovski v Ryuki Matsuda [368] | 6-7,6-2,6-2 | |
| Challenger - Bergamo | 10/30 09:00 | 19 | [213] Mikhail Kukushkin v Kalin Ivanovski [305] | 3-6,7-6,6-4 | |
| Challenger - Bergamo | 10/29 09:00 | 14 | Alessio Balestrieri v Kalin Ivanovski | 2-6,1-6 | |
| Challenger - Hamburg | 10/16 14:00 | 25 | [305] Kalin Ivanovski v Jelle Sels [449] | 2-6,4-6 | |
| Challenger - Bratislava | 10/12 09:00 | 26 | [330] Martin Damm v Kalin Ivanovski [331] | 6-3,6-4 | |
| Challenger - Bratislava | 10/10 10:40 | 25 | [331] Kalin Ivanovski v Peter Gojowczyk [392] | 7-6,6-2 | |
| Challenger - Bratislava | 10/09 08:30 | 19 | [214] Mate Valkusz v Kalin Ivanovski [331] | 3-6,5-7 | |
| Challenger - Bratislava | 10/08 12:25 | 14 | Peter Nad v Kalin Ivanovski | 7-6,2-6,0-6 | |
| ITF - M25 - Setúbal | 09/22 10:00 | 27 | [482] Jaime Faria v Kalin Ivanovski [330] | 6-4,6-4 | |
| ITF - M25 - Setúbal | 09/21 12:30 | 26 | Francisco Rocha v Kalin Ivanovski | 6-7,3-6 | |
| ITF - M25 - Setúbal | 09/19 12:20 | 25 | [448] Sascha Gueymard Wayenburg v Kalin Ivanovski [330] | 4-6,4-6 | |
| ITF - M25 - Sintra | 09/14 09:00 | 26 | [393] Duarte Vale v Kalin Ivanovski [328] | 7-6,6-4 | |
| ITF - M25 - Sintra | 09/13 14:15 | 25 | Marcus Walters v Kalin Ivanovski | 4-6,6-7 | |
| Challenger - Cassis | 09/04 11:15 | 25 | [330] Kalin Ivanovski v Federico Gaio [215] | 6-1,3-6,4-6 | |
| Challenger - Mallorca | 08/30 20:05 | 25 | [259] Joao Sousa v Kalin Ivanovski [330] | 6-4,7-6 | |
| Challenger - Grodzisk Mazowiecki | 08/15 13:35 | 25 | [350] Marius Copil v Kalin Ivanovski [308] | 6-4,1-6,6-4 | |
| Challenger - Banja Luka | 08/08 10:30 | 25 | [300] Clement Tabur v Kalin Ivanovski [306] | 7-6,7-6 | |
| ITF - M25 - Kramsach | 07/30 10:00 | 29 | Gerard Campana Lee v Kalin Ivanovski | 2-6,2-6 | |
| ITF - M25 - Kramsach | 07/29 10:00 | 28 | [341] Mathys Erhard v Kalin Ivanovski [335] | 6-4,2-6,2-6 | |
| ITF - M25 - Kramsach | 07/28 09:00 | 27 | [411] Sandro Kopp v Kalin Ivanovski [335] | 6-7,4-6 | |
| ITF - M25 - Kramsach | 07/27 12:15 | 26 | Syl Gaxherri v Kalin Ivanovski | 1-6,2-6 | |
| ITF - M25 - Kramsach | 07/25 15:00 | 25 | Peter Goldsteiner v Kalin Ivanovski | 1-6,0-6 | |
| ITF - M25 - Telfs | 07/18 08:20 | 25 | Kalin Ivanovski v Nicolas Parizzia | 6-7,3-6 |