Stadium: Court 3 Round: 27 Ground: Carpet indoor
| ITF M15 Opava | 2019/10/31 09:00 | Nik Razborsek v Pospisil, Jaroslav | 5-7,5-7 |
| ITF M15 Opava | 2019/10/30 09:00 | Piotr Grynkowski v Pospisil, Jaroslav | 6-7,0-6 |
| Olomouc, Singles M-ITF-CZE-07A | 2019/10/20 08:00 | Stanek, Robin v Pospisil, Jaroslav | 6-3,6-4 |
| Olomouc, Singles M-ITF-CZE-07A | 2019/10/19 09:30 | Niels Lootsma v Pospisil, Jaroslav | 6-7,2-6 |
| Olomouc, Singles M-ITF-CZE-07A | 2019/10/18 09:50 | Pospisil, Jaroslav v Zsombor Piros | 7-6,4-6,6-3 |
| Olomouc, Singles M-ITF-CZE-07A | 2019/10/17 12:50 | Pospisil, Jaroslav v Martin Krumich | 6-1,6-3 |
| Olomouc, Singles M-ITF-CZE-07A | 2019/10/16 11:25 | Pospisil, Jaroslav v Szic, Sandro | 6-2,6-3 |
| ITF M25 Ricany | 2019/09/25 10:20 | Jonas Forejtek v Pospisil, Jaroslav | 6-3,3-6,6-3 |
| ITF M15 Opava | 2019/10/31 12:30 | Dembek, Michal v Paulson, Andrew | 6-4,7-6 |
| ITF M15 Opava | 2019/10/30 17:15 | Federico Arnaboldi v Dembek, Michal | 3-6,2-6 |
| Liberec, Simples M-ITF-CZE-08A | 2019/10/26 09:55 | Paulson, Andrew v Dembek, Michal | 6-0,1-6,6-4 |
| Liberec, Simples M-ITF-CZE-08A | 2019/10/25 10:30 | Dembek, Michal v Ignatik, Uladzimir | 7-6,7-6 |
| Liberec, Simples M-ITF-CZE-08A | 2019/10/24 11:45 | Dembek, Michal v Stepanek, Antonin | 6-4,6-2 |
| Liberec, Simples M-ITF-CZE-08A | 2019/10/23 12:40 | Dembek, Michal v Domagoj Biljesko | 6-1,6-2 |
| ITF - M15 Sharm El Sheikh | 2019/10/11 08:00 | Dembek, Michal v Marek Gengel | 1-6,6-7 |
| ITF - M15 Sharm El Sheikh | 2019/10/10 09:00 | Dembek, Michal v Luca Potenza | 6-4,3-6,6-4 |