Stadium: Court 3 Round: 28 Ground: Hardcourt outdoor
| ITF - M15 Sharm El Sheikh | 2020/03/06 08:00 | Uzhylovsky, Vladimir v Pospisil, Jaroslav | 4-6,6-2,2-6 |
| ITF - M15 Sharm El Sheikh | 2020/03/05 09:35 | Pospisil, Jaroslav v Capecchi, Daniele | 6-2,6-3 |
| ITF - M15 Sharm El Sheikh | 2020/03/04 08:00 | Seita Watanabe v Pospisil, Jaroslav | 3-6,1-6 |
| Challenger - Cherbourg | 2020/02/09 09:30 | Vit Kopriva v Pospisil, Jaroslav | 6-2,6-2 |
| Challenger - Quimper | 2020/01/27 09:00 | Lorenzo Musetti v Pospisil, Jaroslav | 6-7,6-4,6-4 |
| Helsinki, Finland | 2019/11/13 12:30 | Pospisil, Jaroslav v Nikola Milojevic | 0-6,6-4,3-6 |
| Helsinki, Finland | 2019/11/12 14:35 | Pospisil, Jaroslav v Igor Sijsling | 7-5,6-2 |
| Helsinki, Finland | 2019/11/11 11:00 | Drzewiecki, Karol v Pospisil, Jaroslav | 4-6,0-6 |
| ITF - M15 Sharm El Sheikh | 2020/03/06 08:00 | Kelsey Stevenson v Diego F Flores | 6-2,3-6,6-0 |
| ITF - M15 Sharm El Sheikh | 2020/03/05 08:00 | David Pichler v Kelsey Stevenson | 2-6,3-6 |
| ITF - M15 Sharm El Sheikh | 2020/03/04 13:55 | Ivanov, Simon Anthony v Kelsey Stevenson | 4-6,4-6 |
| ITF - M15 Sharm El Sheikh | 2020/02/26 13:20 | Federico Iannaccone v Kelsey Stevenson | 6-3,6-1 |
| ITF - M15 Sharm El Sheikh | 2020/02/20 09:50 | Kelsey Stevenson v Ryan Nijboer | 3-6,7-6,3-6 |
| ITF - M15 Sharm El Sheikh | 2020/02/19 07:50 | Asrawy, Amr v Kelsey Stevenson | 1-6,4-6 |
| ITF - M15 Sharm El Sheikh | 2020/02/12 11:45 | Kelsey Stevenson v Louis Tessa | 4-6,7-5,2-6 |
| Nonthaburi, Simples M-ITF-THA-06A | 2019/12/04 04:05 | Kelsey Stevenson v Dominik Palan | 7-5,4-6,4-6 |