Round: 25 Ground: Hardcourt outdoor
| ITF Czech Republic F9 | 2016/10/26 08:00 | Nema, Patrik v Pospisil, Jaroslav | 6-3,6-7,6-3 |
| ITF Croatia F11 | 2016/10/22 08:00 | Ternar, Tomislav v Pospisil, Jaroslav | 3-6,6-0,3-6 |
| ITF Croatia F11 | 2016/10/21 08:00 | Paul Woerner v Pospisil, Jaroslav | 4-6,3-6 |
| ITF Croatia F11 | 2016/10/20 10:20 | Obert, Adrian v Pospisil, Jaroslav | 6-7,1-6 |
| ITF Croatia F11 | 2016/10/18 09:45 | Nerman Fatic v Pospisil, Jaroslav | 5-7,3-6 |
| ITF Croatia F10 | 2016/10/13 08:00 | Licciardi, Pietro v Pospisil, Jaroslav | 6-3,5-7,6-4 |
| ITF Croatia F10 | 2016/10/12 09:00 | Khunarikov, Ruslan v Pospisil, Jaroslav | 0-6,1-6 |
| ITF Egypt F26 | 2016/10/02 08:00 | Federico Zeballos v Pospisil, Jaroslav | 3-6,6-3,1-6 |
| ITF Great Britain F6 | 2016/11/10 10:30 | Gabb, Richard v Callahan, Hunter | 6-2,1-6,4-6 |
| ITF Great Britain F6 | 2016/11/09 14:15 | Gabb, Richard v Sizya Ernest Kivanda | 6-4,6-1 |
| ITF Great Britain F5 | 2016/11/04 13:20 | Authom, Maxime v Gabb, Richard | 6-1,6-1 |
| ITF Great Britain F5 | 2016/11/03 10:00 | Gabb, Richard v Faivre, Pierre | 7-6,6-4 |
| ITF Great Britain F5 | 2016/11/02 12:10 | Gabb, Richard v Billy Harris | 5-7,6-4,7-6 |
| ITF Great Britain F5 | 2016/11/01 11:00 | Gabb, Richard v Frost, Matt | 6-3,6-1 |
| ITF Portugal F10 | 2016/07/30 08:30 | Ocleppo, Julian v Gabb, Richard | 6-3,4-6,7-6 |
| ITF Portugal F10 | 2016/07/28 08:30 | Bourcet, Tony v Gabb, Richard | 3-6,4-6 |