Stadium: Court Central Hard Round: 25 Ground: Hardcourt outdoor
| ITF M15 - Heraklion | 2019/11/13 08:00 | Vasil Kirkov v Petros Tsitsipas | 7-6,7-6 |
| ITF M15 - Heraklion | 2019/11/06 12:55 | Lucas Catarina v Petros Tsitsipas | 6-2,6-4 |
| ITF M25 - Monastir | 2019/10/28 11:00 | Alafia Ayeni v Petros Tsitsipas | 6-3,6-1 |
| ITF M25 - Monastir | 2019/10/27 14:00 | Petros Tsitsipas v Adam Nagoudi | 6-4,6-4 |
| ITF M25 - Monastir | 2019/10/27 10:30 | Buvaysar Gadamauri v Petros Tsitsipas | 3-6,4-6 |
| ITF M25 - Monastir | 2019/10/22 09:00 | Maksim Tikhomirov v Petros Tsitsipas | 6-2,1-6,6-1 |
| ITF M25 - Monastir | 2019/10/21 09:00 | Petros Tsitsipas v Buvaysar Gadamauri | 6-4,6-3 |
| ITF M15 - Antalya | 2019/10/08 07:00 | Petros Tsitsipas v Philip Bachmaier | 7-6,6-7,8-10 |
| ITF M15 - Heraklion | 2019/11/12 07:30 | Simon A Ivanov v Filippo Moroni | 6-3,1-6,3-10 |
| ITF M15 - Heraklion | 2019/11/11 08:00 | Simon A Ivanov v Glenn Smits | 6-1,6-3 |
| ITF M15 - Heraklion | 2019/11/10 07:30 | Simon A Ivanov v Lior Goldenberg | 7-5,6-2 |
| ITF M15 - Heraklion | 2019/11/06 12:55 | Simon A Ivanov v Lenny Hampel | 6-7,0-6 |
| ITF M15 - Heraklion | 2019/11/05 07:30 | Simon A Ivanov v Tadas Tarasevicius | 6-1,6-4 |
| ITF M15 - Heraklion | 2019/11/04 08:00 | Simon A Ivanov v Stephanos Schinas | 7-6,6-3 |
| ITF M15 Burgas | 2019/10/11 10:25 | Fabrizio Ornago v Simon A Ivanov | 6-2,6-0 |
| ITF M15 Burgas | 2019/10/10 10:10 | Simon A Ivanov v Vasko Mladenov | 3-6,6-2,6-2 |