Stadium: Court 4 Round: 27 Ground: Clay
| ITF M25 Kursumlijska Banja | 2023/05/11 08:30 | Timo Legout v Kalin Ivanovski | 6-2,1-6,0-6 |
| ITF M25 Kursumlijska Banja | 2023/05/10 09:00 | Kalin Ivanovski v Viktor Jovic | 3-6,6-3,6-4 |
| Challenger Prague | 2023/05/01 13:00 | Kalin Ivanovski v Dominic Stephan Stricker | 2-6,2-6 |
| Challenger Oeiras | 2023/04/16 12:30 | Billy Harris v Kalin Ivanovski | 6-2,4-6,6-4 |
| Challenger Split | 2023/04/11 12:20 | Duje Ajdukovic v Kalin Ivanovski | 6-7,6-1,6-1 |
| ITF M25 Dubrovnik | 2023/04/06 08:00 | Aldin Setkic v Kalin Ivanovski | 7-6,6-2 |
| ITF M25 Dubrovnik | 2023/04/05 07:00 | Matteo Donati v Kalin Ivanovski | 6-1,3-6,0-6 |
| ITF M25 Toulouse | 2023/03/23 10:00 | Kalin Ivanovski v Harry Wendelken | 1-6,6-7 |
| ITF M25 Kursumlijska Banja | 2023/05/11 08:30 | Hady Habib v Mathys Erhard | 6-2,7-5 |
| ITF M25 Kursumlijska Banja | 2023/05/10 09:15 | Mili Poljicak v Hady Habib | 6-3,3-6,1-6 |
| ITF M15 Kursumlijska Banja | 2023/05/02 13:05 | Hady Habib v Adriano Dzhenev | 6-7,1-6 |
| ITF M25 Jakarta | 2023/04/18 07:15 | Hady Habib v Tristan Schoolkate | 3-6,6-2,4-6 |
| ITF M25 Jakarta | 2023/04/13 02:30 | Yunseok Jang v Hady Habib | 6-4,3-6,6-0 |
| ITF M25 Jakarta | 2023/04/12 02:00 | Hady Habib v Maximus Jones | 6-4,6-7,6-4 |
| ITF M15 Monastir | 2023/03/14 08:30 | Hady Habib v Tomasz Berkieta | 3-6,4-6 |
| ITF M15 Monastir | 2023/03/10 08:30 | Hady Habib v Stefano Napolitano | 6-4,3-6,3-6 |