Stadium: COURT VIKTOR TROICKI Round: 62 Ground: Clay
| ITF M15 Kursumlijska Banja | 2023/06/02 10:30 | Alvaro Guillen Meza v Milan Drinic | 6-2,3-6,7-6 |
| ITF M15 Kursumlijska Banja | 2023/06/01 07:30 | Nikita Mashtakov v Milan Drinic | 2-6,1-6 |
| ITF M15 Kursumlijska Banja | 2023/05/31 07:00 | Milan Drinic v Tomas Farjat | 6-4,6-2 |
| ITF M15 Kursumlijska Banja | 2023/05/30 10:20 | Milan Drinic v Nicolas Villalon | 4-6,6-1,2-10 |
| ITF M15 Kursumlijska Banja | 2023/05/28 14:00 | Bautista Vilicich v Milan Drinic | 5-7,6-4,8-10 |
| ITF M15 Brcko | 2023/05/23 07:30 | Igor Gimenez v Milan Drinic | 7-6,6-4 |
| ITF M15 Brcko | 2023/05/22 13:00 | Vitali Shvets v Milan Drinic | 1-6,3-6 |
| ITF M25 Kursumlijska Banja | 2023/05/19 10:10 | Milan Drinic v Mikalai Haliak | 3-6,3-6 |
| ITF M15 Kursumlijska Banja | 2023/06/01 11:30 | Peter Fajta v Novak Novakovic | 6-1,7-6 |
| ITF M15 Kursumlijska Banja | 2023/05/31 07:00 | Novak Novakovic v Nicolas Buitrago | 0-6,7-5,6-4 |
| ITF M15 Kursumlijska Banja | 2023/05/30 10:50 | Novak Novakovic v Gorazd Srbljak | 6-4,6-3 |
| ITF M15 Kursumlijska Banja | 2023/05/29 11:40 | Petr Bar Biryukov v Novak Novakovic | 6-3,3-6,3-10 |
| ITF M25 Kursumlijska Banja | 2023/05/17 13:05 | Novak Novakovic v Mark Lajal | 0-6,4-6 |
| ITF M25 Kursumlijska Banja | 2023/05/16 08:30 | Vanja Petrov v Novak Novakovic | 7-6,3-6,4-10 |
| ITF M25 Kursumlijska Banja | 2023/05/15 12:55 | Tonghan Gu v Novak Novakovic | 4-6,0-6 |
| UTR Pro Tennis Series Dubai | 2022/12/10 08:00 | Novak Novakovic v Matyas Fuele | 4-6,4-5 |