Stadium: Court 1 (Center) Round: 26 Ground: Clay
| ITF M25 Skopje | 2023/06/07 12:15 | Ivanovski, Kalin v Colson, Tibo | 4-6,6-2,6-4 |
| Challenger Skopje | 2023/05/23 10:00 | Ivanovski, Kalin v Prizmic, Dino | 4-6,1-6 |
| ITF M25 Kursumlijska Banja | 2023/05/18 13:00 | 할리아크, 미칼라이 v Ivanovski, Kalin | 6-4,1-6,6-3 |
| ITF M25 Kursumlijska Banja | 2023/05/14 10:45 | 타부르, 클레멘트 v Ivanovski, Kalin | 6-4,3-6,6-2 |
| ITF M25 Kursumlijska Banja | 2023/05/13 08:00 | 오브샤렌코, 올렉산들 v Ivanovski, Kalin | 5-7,2-6 |
| ITF M25 Kursumlijska Banja | 2023/05/12 08:00 | Ivanovski, Kalin v 하비브, 하디 | 7-6,7-5 |
| ITF M25 Kursumlijska Banja | 2023/05/11 08:30 | 레그아웃, 티모 v Ivanovski, Kalin | 6-2,1-6,0-6 |
| ITF M25 Kursumlijska Banja | 2023/05/10 09:00 | Ivanovski, Kalin v Viktor Jovic | 3-6,6-3,6-4 |
| ITF M25 Skopje | 2023/06/07 12:25 | Hans Albert Schubert v Bill, Alen | 3-6,1-6 |
| ITF M25 Skopje | 2023/06/06 07:30 | Bill, Alen v Veljko Krstic | 6-4,6-2 |
| ITF M25 Skopje | 2023/06/05 08:00 | Bill, Alen v Johannes Prammer | 6-1,6-1 |
| ITF M25 Skopje | 2023/06/04 09:30 | Bill, Alen v Boris Stojanovic | 6-1,6-1 |
| ITF M15 Prijedor | 2023/05/15 11:30 | Bill, Alen v Habib, Ali | 7-6,2-6,7-10 |
| ITF M15 Doboj | 2023/05/08 10:30 | Bill, Alen v Basic, Nikola | 2-6,4-6 |
| ITF M15 Doboj | 2023/05/07 10:30 | Dzenan Bakovic v Bill, Alen | 2-6,3-6 |
| ITF M15 Osijek | 2023/05/01 10:10 | Radomir Tomic v Bill, Alen | 6-0,6-3 |