Stadium: Court 1 Round: 44 Ground: Clay
| Jounieh, Singles M-ITF-LBN-02A | 2019/09/23 11:00 | Petros Tsitsipas v Yazbeck, Jean-Marie | 6-0,6-0 |
| Trieste, Singles M-ITF-ITA-20A | 2019/09/02 08:00 | Luca Tomasetto v Petros Tsitsipas | 6-4,6-2 |
| Trieste, Singles M-ITF-ITA-20A | 2019/09/01 09:30 | Dominique Graf v Petros Tsitsipas | 6-7,7-6,5-10 |
| ITF - M15 Héraklion | 2019/05/29 09:10 | Paris, Joshua v Petros Tsitsipas | 5-7,6-4,6-4 |
| ITF - M15 Héraklion | 2019/05/22 11:35 | Hoyt, Evan v Petros Tsitsipas | 6-2,6-4 |
| ITF - M15 Héraklion | 2019/05/13 09:00 | Murphy, Brandon v Petros Tsitsipas | 7-6,6-4 |
| ITF - M15 Héraklion | 2019/05/09 07:00 | Dembek, Michal v Petros Tsitsipas | 6-4,6-4 |
| ITF - M15 Héraklion | 2019/05/07 10:00 | Shumeiko, Pavel v Petros Tsitsipas | 3-6,4-6 |
| Jounieh, Singles M-ITF-LBN-02A | 2019/09/23 08:00 | Abou Boutros, Alexander v Rajic, Dusan | 2-6,2-6 |
| ITF M15 Zlatibor | 2019/09/15 06:30 | Roko Horvat v Rajic, Dusan | 6-2,6-3 |
| Brasov, Singles Qualifying M-ITF-ROU-04A | 2019/09/10 09:15 | Kijametovic, Aziz v Rajic, Dusan | 6-4,6-2 |
| Brasov, Singles Qualifying M-ITF-ROU-04A | 2019/09/09 07:00 | Egor Matvievici v Rajic, Dusan | 1-6,4-6 |
| ITF M15 Curtea de Arges | 2019/08/20 08:20 | Luncanu, Petru-Alexandru v Rajic, Dusan | 7-5,6-2 |
| Baja, Singles Qualifying M-ITF-HUN-03A | 2019/08/13 09:30 | Rajic, Dusan v Daniel Paty | 7-6,5-7,9-11 |
| ITF M15 Novi Sad | 2019/08/05 10:30 | Rajic, Dusan v Micov, Stefan | 3-6,3-6 |
| ITF M15 Novi Sad | 2019/07/29 10:30 | Rajic, Dusan v Hodor, Samuel | 1-6,3-6 |