Stadium: Court 5 Round: 14 Ground: Clay
| Challenger - Troyes | 2023/07/02 12:10 | Kalin Ivanovski v Giuseppe Tresca | 4-6,6-7 |
| Challenger - Poznań | 2023/06/18 08:30 | Kai Wehnelt v Kalin Ivanovski | 6-3,3-6,6-3 |
| Davis Cup | 2023/06/15 10:00 | Kalin Ivanovski v Alexander Cozbinov | 5-7,2-5 |
| Davis Cup | 2023/06/14 10:35 | Kalin Ivanovski v Liam Delicata | 6-2,6-4 |
| ITF M25 Skopje | 2023/06/11 11:00 | Kalin Ivanovski v Sascha Gueymard Wayenburg | 7-6,6-4 |
| ITF M25 Skopje | 2023/06/10 12:40 | Ergi Kirkin v Kalin Ivanovski | 6-3,2-6,2-6 |
| ITF M25 Skopje | 2023/06/08 11:50 | Kalin Ivanovski v Alen Bill | 6-0,6-0 |
| ITF M25 Skopje | 2023/06/07 12:15 | Kalin Ivanovski v Tibo Colson | 4-6,6-2,6-4 |
| ITF M15 - Wrocław | 2023/06/28 12:50 | Filip Kosinski v Brandon Walkin | 2-6,0-6 |
| ITF - M25 Poprad | 2023/06/20 09:40 | Brandon Walkin v Vladyslav Orlov | 3-6,4-6 |
| ITF M15 - Sarajevo | 2023/06/08 07:00 | Brandon Walkin v Dusan Obradovic | 6-3,6-7,4-6 |
| ITF M15 - Sarajevo | 2023/06/07 07:00 | Bozo Barun v Brandon Walkin | 4-6,2-6 |
| ITF - M25 Kiseljak | 2023/05/31 10:55 | Brandon Walkin v Kirill Kivattsev | 6-7,6-7 |
| ITF - M25 Kiseljak | 2023/05/30 09:05 | Brandon Walkin v Gal Emersic Potocnik | 7-5,6-0 |
| ITF - M25 Kiseljak | 2023/05/29 09:30 | Brandon Walkin v Lukas Rohseano | 6-2,6-1 |
| ITF - M15 Brčko | 2023/05/24 07:30 | Brandon Walkin v Kirill Kivattsev | 6-2,4-6,4-6 |