| Prostejov, Czech Republic | 06/04 08:00 | 14 | [329] Pospisil, Jaroslav v Edoardo Lavagno [297] | 0-6,2-6 | |
| Challenger Manama | 02/12 10:05 | 14 | [338] Vitaliy Sachko v Pospisil, Jaroslav [333] | 6-4,6-3 | |
| Parma II, Italy | 10/02 12:50 | 14 | [318] Pospisil, Jaroslav v Oleksandr Ovcharenko [437] | 3-6,5-7 | |
| Challenger Blois | 06/12 08:30 | 14 | Thiago Seyboth Wild v Pospisil, Jaroslav | 6-4,6-3 | |
| Challenger - Oeiras | 03/28 09:30 | 19 | Pospisil, Jaroslav v Noah Rubin | 1-6,5-7 | |
| Challenger - Oeiras | 03/27 11:40 | 14 | Madaras, Dragos Nicolae v Pospisil, Jaroslav | 3-6,3-6 | |
| Bengaluru 2, India, Qualifying | 02/13 04:00 | 14 | Kalovelonis, Markos v Pospisil, Jaroslav | 6-4,3-6,6-3 | |
| Challenger - Bengaluru | 02/06 06:10 | 14 | Gojo, Borna v Pospisil, Jaroslav | 7-6,3-6,6-4 | |
| Challenger Bendigo | 01/04 23:00 | 25 | Zizou Bergs v Pospisil, Jaroslav | 6-1,7-6 | |
| Challenger Bendigo | 01/03 04:25 | 24 | Pospisil, Jaroslav v Matthew C Romios | 6-2,6-3 | |
| Challenger Lima | 10/26 18:35 | 25 | Andrea Collarini v Pospisil, Jaroslav | 6-1,6-4 | |
| Challenger Lima | 10/25 17:00 | - | Alexis Galarneau v Pospisil, Jaroslav | 4-6,4-6 | |
| Challenger Lima | 10/24 21:10 | 26 | Pospisil, Jaroslav v Hidalgo, Diego | 4-6,6-3,6-3 | |
| Bogota, Colombia | 10/19 15:00 | 25 | Gomez, Alejandro v Pospisil, Jaroslav | 6-3,3-6,7-5 | |
| Bogota, Colombia | 10/18 15:00 | 19 | Stevens, Bart v Pospisil, Jaroslav | 6-3,6-7,3-6 | |
| Bogota, Colombia | 10/17 15:00 | 14 | Pospisil, Jaroslav v Thirouin, Jean | 6-4,6-7,6-2 | |
| ITF M25 Budapest | 09/29 11:10 | 25 | Gergely Madarasz v Pospisil, Jaroslav | 6-4,1-6,7-5 | |
| Prostejov, Singles M-ITF-CZE-04A | 08/16 10:50 | 25 | Pospisil, Jaroslav v Alvarez Varona, Nicolas | 3-6,3-6 | |
| Challenger Meerbusch | 08/08 10:00 | 14 | Duje Ajdukovic v Pospisil, Jaroslav | 6-3,6-2 | |
| Challenger Liberec | 08/01 15:00 | 14 | Alexander Ritschard v Pospisil, Jaroslav | 6-2,6-4 | |
| ITF M15 Poprad | 07/08 07:55 | 26 | Milos Karol v Pospisil, Jaroslav | 6-4,7-6 | |
| ITF M15 Poprad | 07/07 08:00 | 25 | Peter Nad v Pospisil, Jaroslav | Retired | |
| Czech Extraliga, Men | 12/13 10:00 | - | Pospisil, Jaroslav v Vojtech Vlkovsky | 6-2,6-3 | |
| Marbella, Spain | 10/24 09:40 | 19 | Pospisil, Jaroslav v Carlos Gimeno Valero | Cancelled | |
| ITF M25 Pardubice | 09/30 10:30 | 44 | Pedro Cachin v Pospisil, Jaroslav | 6-3,6-4 | |
| ITF M25 Pardubice | 09/30 07:00 | 44 | Pospisil, Jaroslav v Zukas, Matias | 6-1,6-2 | |
| ITF M25 Prague | 09/16 08:00 | 25 | [320] Vit Kopriva v Pospisil, Jaroslav [486] | 6-1,6-3 | |
| ITF M25 Prague | 09/15 10:10 | 44 | [406] Yshai Oliel v Pospisil, Jaroslav [486] | 7-5,6-2 | |
| ITF M25 Prague | 09/14 10:30 | 44 | Paroulek, Tadeas v Pospisil, Jaroslav | 3-6,7-5,2-10 | |
| ITF M25 Prague | 09/13 11:00 | 44 | Pospisil, Jaroslav v Zopp, Jurgen | 7-6,6-1 |