Stadium: Court 2 Round: 27 Ground: Clay
| ITF M15 Zlatibor | 2019/09/19 09:30 | Celebic, Ljubomir v Kranic, Karlo | 4-6,5-7 |
| ITF M15 Zlatibor | 2019/09/18 07:30 | Kranic, Karlo v Gergely Madarasz | 7-6,7-5 |
| ITF M15 Zlatibor | 2019/09/17 08:40 | Kranic, Karlo v Subanovic, Nemanja | 6-2,6-2 |
| ITF M15 Zlatibor | 2019/09/16 10:30 | Kranic, Karlo v Aleksa Ciric | 6-2,6-2 |
| Varna, Singles M-ITF-BUL-04A | 2019/09/14 07:00 | Kranic, Karlo v Galarza, Juan Ignacio | 1-6,1-6 |
| Varna, Singles M-ITF-BUL-04A | 2019/09/13 07:00 | Denis Klok v Kranic, Karlo | 3-6,3-6 |
| Varna, Singles M-ITF-BUL-04A | 2019/09/12 08:40 | Ontica, Cosmin v Kranic, Karlo | 5-7,1-6 |
| Varna, Singles M-ITF-BUL-04A | 2019/09/10 06:30 | Kranic, Karlo v Dittmer, Philipp | 6-1,6-2 |
| ITF M15 Zlatibor | 2019/09/19 08:30 | Matyas Fuele v Miladinovic, Marko | 6-7,0-6 |
| ITF M15 Zlatibor | 2019/09/18 07:30 | Shendrit Deari v Miladinovic, Marko | 1-6,6-7 |
| Challenger Banja Luka | 2019/09/12 12:00 | Miladinovic, Marko v Dmitry Popko | 6-7,6-3,2-6 |
| Challenger Banja Luka | 2019/09/11 14:10 | Nikola Milojevic v Miladinovic, Marko | 2-6,2-6 |
| Challenger Banja Luka | 2019/09/10 10:00 | Miladinovic, Marko v Tomas Martin Etcheverry | 6-2,5-7,7-6 |
| Gyor, Qualifications Simples M-ITF-HUN-04A | 2019/08/30 08:00 | Miladinovic, Marko v Camilo Ugo Carabelli | 3-6,4-6 |
| Gyor, Qualifications Simples M-ITF-HUN-04A | 2019/08/29 10:15 | Nagy, Peter v Miladinovic, Marko | 1-6,3-6 |
| ITF M15 Novi Sad | 2019/08/18 08:00 | Yshai Oliel v Miladinovic, Marko | 6-2,1-6,2-6 |