Stadium: Court 1 Round: 44 Ground: Clay
| ITF M25 - Jounieh | 2019/09/23 11:00 | Petros Tsitsipas v Jean-Marie Yazbeck | 6-0,6-0 |
| ITF M25 - Trieste | 2019/09/02 08:00 | Luca Tomasetto v Petros Tsitsipas | 6-4,6-2 |
| ITF M25 - Trieste | 2019/09/01 09:30 | Dominique Graf v Petros Tsitsipas | 6-7,7-6,5-10 |
| ITF M15 - Heraklion | 2019/05/29 09:10 | Joshua Paris v Petros Tsitsipas | 5-7,6-4,6-4 |
| ITF M15 - Heraklion | 2019/05/22 11:35 | Evan Hoyt v Petros Tsitsipas | 6-2,6-4 |
| ITF M15 - Heraklion | 2019/05/13 09:00 | Brandon Murphy v Petros Tsitsipas | 7-6,6-4 |
| ITF M15 - Heraklion | 2019/05/09 07:00 | Michal Dembek v Petros Tsitsipas | 6-4,6-4 |
| ITF M15 - Heraklion | 2019/05/07 10:00 | Pavel Shumeiko v Petros Tsitsipas | 3-6,4-6 |
| ITF M25 - Jounieh | 2019/09/23 08:00 | Alexander Abou Boutros v Dusan Rajic | 2-6,2-6 |
| ITF M15 - Zlatibor | 2019/09/15 06:30 | Roko Horvat v Dusan Rajic | 6-2,6-3 |
| ITF M15 - Brasov | 2019/09/10 09:15 | Aziz Kijametovic v Dusan Rajic | 6-4,6-2 |
| ITF M15 - Brasov | 2019/09/09 07:00 | Egor Matvievici v Dusan Rajic | 1-6,4-6 |
| ITF M15 - Curtea de Arges | 2019/08/20 08:20 | Petru-Alexandru Luncanu v Dusan Rajic | 7-5,6-2 |
| ITF M15 - Baja | 2019/08/13 09:30 | Dusan Rajic v Daniel Paty | 7-6,5-7,9-11 |
| ITF M15 - Novi Sad | 2019/08/05 10:30 | Dusan Rajic v Stefan Micov | 3-6,3-6 |
| ITF M15 - Novi Sad | 2019/07/29 10:30 | Dusan Rajic v Samuel Hodor | 1-6,3-6 |