Stadium: Court 3 Round: 2
| 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 M25 Kursumlijska Banja | 2023/05/18 13:00 | Mikalai Haliak v Kalin Ivanovski | 6-4,1-6,6-3 |
| ITF M25 Kursumlijska Banja | 2023/05/14 10:45 | Clement Tabur v Kalin Ivanovski | 6-4,3-6,6-2 |
| ITF M25 Kursumlijska Banja | 2023/05/13 08:00 | Oleksandr Ovcharenko v Kalin Ivanovski | 5-7,2-6 |
| ITF M15 Monastir | 2023/04/05 09:10 | Daniel Rodrigues v Liam Delicata | 6-4,6-1 |
| ITF M15 Monastir | 2023/03/28 10:00 | Luca Wiedenmann v Liam Delicata | 6-2,6-2 |
| Davis Cup | 2022/07/28 07:20 | Liam Delicata v Tamerlan Azizov | 6-1,3-6,4-6 |
| ITF M15 Antalya | 2021/11/07 06:30 | Liam Delicata v Luca Fantini | 7-6,2-6,3-10 |
| Davis Cup | 2021/06/18 09:20 | Osgar O'Hoisin v Liam Delicata | 6-4,6-2 |
| Davis Cup | 2021/06/17 09:05 | Raphael Calzi v Liam Delicata | 6-3,6-4 |
| Davis Cup | 2021/06/16 09:05 | Lucas Catarina v Liam Delicata | 6-0,6-1 |