Stadium: Court 1 Round: 14 Ground: Clay
| Challenger - Poznan | 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 |
| Challenger - Skopje | 2023/05/23 10:00 | Kalin Ivanovski v Dino Prizmic | 4-6,1-6 |
| ITF - M15 Bergamo | 2023/06/27 09:20 | Giuseppe Tresca v Alexandr Binda | 2-6,3-6 |
| ITF - M25 Cattolica | 2023/06/19 21:15 | Samuel Vincent Ruggeri v Giuseppe Tresca | 6-4,6-3 |
| ITF - M15 Chieti | 2023/06/13 11:15 | Gianluca Di Nicola v Giuseppe Tresca | 7-6,6-2 |
| ITF - M15 Frascati | 2023/06/05 12:35 | Giuseppe Tresca v Mariano Tammaro | 7-6,3-6,2-10 |
| ITF - M15 Constanta | 2023/05/31 10:25 | Cezar Cretu v Giuseppe Tresca | 6-2,6-0 |
| ITF - M15 Constanta | 2023/05/30 08:25 | Giuseppe Tresca v Luca Matteo Sobbe | 7-5,6-4 |
| ITF - M15 Pazardžik | 2023/05/22 12:00 | Giuseppe Tresca v Peetu Pohjola | 2-6,2-6 |
| ITF - M15 Pazardžik | 2023/05/22 07:00 | Giuseppe Tresca v David Simeonov | 7-5,6-3 |