Stadium: Court 2 Round: 44 Ground: Clay
| 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 M15 Grasse | 2019/04/29 14:30 | Florent Bax v Petros Tsitsipas | 6-4,6-2 |