Stadium: Center Court Round: 62 Ground: Clay
| Eastern European Championship | 2020/07/14 18:00 | Milan Drinic v Pavle Daljev | 6-4,3-6,6-7 |
| UTR Pro Beograd | 2023/04/15 09:52 | Milan Drinic v Stefan Popovic | 1-6,1-6 |
| UTR Pro Beograd | 2023/04/14 07:00 | Milan Drinic v Kristian Juhas | 3-6,6-1,6-4 |
| UTR Pro Beograd | 2023/04/12 08:00 | Milan Drinic v Aleksa Pisaric | 6-4,2-6,6-3 |
| UTR Pro Beograd | 2023/04/11 09:00 | Milan Drinic v Petr Nesterov | 3-6,3-6 |
| ITF M25 Opatija | 2023/03/19 08:00 | Milan Drinic v Maks Lukman | 6-7,6-2,10-12 |
| ITF M15 Rovinj | 2023/03/16 09:00 | Federico Arnaboldi v Milan Drinic | 7-6,7-6 |
| ITF M15 Rovinj | 2023/03/15 12:55 | Milan Drinic v Lucas Bouquet | 6-4,6-4 |
| ITF M15 Rovinj | 2023/03/15 08:30 | Noah Perfetti v Milan Drinic | 1-6,3-6 |
| ITF M25 Kursumlijska Banja | 2023/05/14 09:30 | Pavle Daljev v Alexandar Balj | 6-1,6-0 |
| ITF M25 Kursumlijska Banja | 2023/05/08 13:05 | Iliyan Radulov v Pavle Daljev | 6-1,6-2 |
| ITF M15 Kursumlijska Banja | 2023/04/23 07:00 | Pavle Daljev v Aleksei Khomich | 3-6,6-4,6-10 |
| ITF M15 Antalya | 2023/03/27 09:50 | Louroi Martinez v Pavle Daljev | 6-2,6-1 |
| ITF M15 Antalya | 2023/03/26 08:00 | Guilherme Meale v Pavle Daljev | 1-6,4-6 |
| ITF M15 Antalya | 2023/03/12 10:30 | Pavle Daljev v Berk Ilkel | 3-6,1-6 |
| ITF M15 Antalya | 2023/01/23 10:15 | Antonio Massara v Pavle Daljev | 6-2,6-3 |
| ITF M25 Antalya | 2022/11/06 05:30 | Rik Muller v Pavle Daljev | 6-2,6-0 |