Stadium: Court Central Hard Round: 25 Ground: Hardcourt outdoor
| ITF - M15 Héraklion | 2019/11/13 08:00 | Kirkov, Vasil v Petros Tsitsipas | 7-6,7-6 |
| ITF - M15 Héraklion | 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 Nagoudi, Adam | 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 | Tikhomirov, Maksim 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 Bachmaier, Philip | 7-6,6-7,8-10 |
| ITF - M15 Héraklion | 2019/11/12 07:30 | Ivanov, Simon Anthony v Moroni, Filippo | 6-3,1-6,3-10 |
| ITF - M15 Héraklion | 2019/11/11 08:00 | Ivanov, Simon Anthony v Smits, Glenn | 6-1,6-3 |
| ITF - M15 Héraklion | 2019/11/10 07:30 | Ivanov, Simon Anthony v Goldenberg, Lior | 7-5,6-2 |
| ITF - M15 Héraklion | 2019/11/06 12:55 | Ivanov, Simon Anthony v Hampel, Lenny | 6-7,0-6 |
| ITF - M15 Héraklion | 2019/11/05 07:30 | Ivanov, Simon Anthony v Tarasevicius, Tadas | 6-1,6-4 |
| ITF - M15 Héraklion | 2019/11/04 08:00 | Ivanov, Simon Anthony v Schinas, Stephanos | 7-6,6-3 |
| Burgas, Singles Qualifying M-ITF-BUL-05A | 2019/10/11 10:25 | Ornago, Fabrizio v Ivanov, Simon Anthony | 6-2,6-0 |
| Burgas, Singles Qualifying M-ITF-BUL-05A | 2019/10/10 10:10 | Ivanov, Simon Anthony v Mladenov, Vasko | 3-6,6-2,6-2 |