Stadium: Court 5 Round: 19 Ground: Clay
| Challenger - Iași | 2023/07/09 10:20 | Kalin Ivanovski v Brandon Walkin | 6-2,6-2 |
| 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 |
| Challenger - Iași | 2023/07/09 12:05 | Dan Alexandru Tomescu v Ilya Snitari | 6-4,6-2 |
| ITF - M25 Brasov | 2023/07/03 13:05 | Radu Mihai Papoe v Dan Alexandru Tomescu | 6-4,6-2 |
| ITF M15 - Belgrado | 2023/06/27 11:40 | Dan Alexandru Tomescu v Vuk Radjenovic | 4-6,6-3,3-6 |
| ITF - M15 Cluj Napoca | 2023/06/21 09:10 | Dan Alexandru Tomescu v Johannes Haerteis | 4-6,2-6 |
| ITF - M15 Constanta | 2023/06/01 08:00 | Dan Alexandru Tomescu v Petr Nesterov | 5-7,3-6 |
| ITF - M15 Constanta | 2023/05/31 07:00 | Dan Alexandru Tomescu v Moerani Bouzige | 6-4,6-3 |
| ITF - M15 Boekarest | 2023/05/26 07:55 | Florent Bax v Dan Alexandru Tomescu | 6-2,6-2 |
| ITF - M15 Boekarest | 2023/05/25 09:45 | Dan Alexandru Tomescu v Vlad Andrei Dancu | 6-3,7-5 |