Stadium: Court 1 (Center) Round: 29 Ground: Clay
| ITF M15 Poitiers | 2023/03/18 13:30 | Kalin Ivanovski v Sascha Gueymard Wayenburg | 2-6,6-7 |
| 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 M25 Kursumlijska Banja | 2023/05/12 08:00 | Kalin Ivanovski v Hady Habib | 7-6,7-5 |
| ITF M25 Skopje | 2023/06/10 08:00 | Sascha Gueymard Wayenburg v Vito Tonejc | 7-6,6-1 |
| ITF M25 Skopje | 2023/06/09 08:00 | Neil Oberleitner v Sascha Gueymard Wayenburg | 1-6,2-6 |
| ITF M25 Skopje | 2023/06/08 08:00 | Davud Amirov v Sascha Gueymard Wayenburg | 3-6,2-6 |
| ITF M25 Skopje | 2023/06/06 09:50 | Ioannis Xilas v Sascha Gueymard Wayenburg | 0-6,2-6 |
| French Open | 2023/05/24 10:25 | Camilo Ugo Carabelli v Sascha Gueymard Wayenburg | 6-2,3-6,6-2 |
| French Open | 2023/05/22 12:30 | Sascha Gueymard Wayenburg v Denis Kudla | 6-4,6-3 |
| ITF M25 Valldoreix | 2023/05/10 08:00 | Benjamin Winter Lopez v Sascha Gueymard Wayenburg | 6-1,6-1 |
| ITF M25 Sabadell | 2023/05/02 11:00 | Sascha Gueymard Wayenburg v Mathias Bourgue | 3-6,0-6 |