Stadium: Center Court Round: 25 Ground: Hardcourt outdoor
| ITF M15 - Heraklion | 2019/05/09 07:00 | Michal Dembek v Petros Tsitsipas | 6-4,6-4 |
| ITF M15 - Antalya | 2019/12/17 07:00 | Michal Dembek v Ivan Nedelko | 7-6,5-7,2-6 |
| ITF M15 Antalya - Kval | 2019/12/09 07:00 | Michal Dembek v Igor Saveljic | 1-6,6-7 |
| ITF - M15 - Monastir | 2019/11/27 12:40 | Michal Dembek v Benjamin Lock | 6-7,2-6 |
| ITF M15 - Prag | 2019/11/06 13:00 | Illya Beloborodko v Michal Dembek | 6-2,7-6 |
| ITF M15 - Opava | 2019/11/01 08:55 | Jaroslav Pospisil v Michal Dembek | 4-6,6-3,6-4 |
| ITF M15 - Opava | 2019/10/31 12:30 | Michal Dembek v Andrew Paulson | 6-4,7-6 |
| ITF M15 - Opava | 2019/10/30 17:15 | Federico Arnaboldi v Michal Dembek | 3-6,2-6 |
| ITF M15 - Liberec | 2019/10/26 09:55 | Andrew Paulson v Michal Dembek | 6-0,1-6,6-4 |
| Challenger Burnie | 2020/01/28 00:35 | Benjamin Lock v Petros Tsitsipas | 4-6,6-2,6-2 |
| Challenger Burnie | 2020/01/26 23:00 | Naoki Tajima v Petros Tsitsipas | 4-6,6-4,4-6 |
| Challenger Bendigo | 2020/01/11 23:00 | Yoshihito Nishioka v Petros Tsitsipas | 6-4,6-4 |
| ITF M15 - Heraklion | 2019/12/10 11:00 | Adrian Bodmer v Petros Tsitsipas | 7-5,6-1 |
| ITF M15 - Heraklion | 2019/12/04 10:55 | Petros Tsitsipas v Matias Zukas | 1-6,4-6 |
| ITF M15 - Heraklion | 2019/11/28 08:00 | Daniel Masur v Petros Tsitsipas | 6-0,6-2 |
| ITF M15 - Heraklion | 2019/11/27 09:30 | Alexander Donski v Petros Tsitsipas | 6-4,4-6,4-6 |
| ITF M15 - Heraklion | 2019/11/20 12:00 | Petros Tsitsipas v Simon A Ivanov | 4-6,3-6 |