| UTR Pro Beograd | 2023/10/01 10:30 | Vuk Radjenovic v Karlo Kajin | 6-2,6-3 |
| UTR Pro Tennis Series Zadar | 2022/05/31 07:30 | Dmitrii Vasilev v Karlo Kajin | 3-6,7-6,2-0 |
| UTR Pro Tennis Series Zadar | 2022/05/30 06:00 | Karlo Kajin v Maximilian Homberg | 4-6,2-6 |
| UTR Pro Tennis Series Zadar | 2021/07/04 08:30 | Jerko Brkic v Karlo Kajin | 6-4,6-4 |
| UTR Pro Tennis Series Zadar | 2021/07/03 11:30 | Ihor Dudun v Karlo Kajin | 3-6,1-6 |
| UTR Pro Tennis Series Zadar | 2021/07/01 11:00 | Karlo Kajin v Matija Pecotic | 1-6,2-5 |
| UTR Pro Tennis Series Zadar | 2021/06/30 09:30 | Karlo Kajin v Alexander Kiefer | 3-6,1-6 |
| UTR Pro Tennis Series Zadar | 2021/06/29 12:30 | Karlo Kajin v Aleksei Khomich | 6-4,3-6,2-6 |
| UTR Pro Beograd | 2023/10/01 09:43 | Milan Drinic v Obrad Markovski | 2-6,5-7 |
| ITF M15 Kursumlijska Banja | 2023/09/20 11:25 | Milan Drinic v Ioannis Kountourakis | 4-6,6-3,4-6 |
| ITF M15 Kursumlijska Banja | 2023/09/13 13:20 | Dusan Obradovic v Milan Drinic | 7-5,3-6,6-1 |
| ITF M15 Pirot | 2023/09/05 12:55 | Filip Cristian Jianu v Milan Drinic | 4-6,6-4,6-4 |
| ITF M15 Kursumlijska Banja | 2023/08/30 10:30 | Milan Drinic v Peter Fajta | 3-6,6-3,6-7 |
| ITF M25 Osijek | 2023/08/10 09:45 | Milan Drinic v Sebastian Prechtel | 5-7,7-6,2-6 |
| ITF M25 Osijek | 2023/08/08 10:55 | Viktor Jovic v Milan Drinic | 2-6,3-6 |
| ITF M15 Novi Sad | 2023/08/01 11:10 | Kristijan Juhas v Milan Drinic | 6-3,1-6,13-11 |