Round: 25 Ground: Clay
| ITF Serbia F7 | 2016/09/16 09:00 | Alexandar Lazarov v Maciej Rajski | 1-6,6-4,6-2 |
| ITF Serbia F7 | 2016/09/15 08:00 | Maciej Rajski v Borna Gojo | 6-4,7-6 |
| ITF Serbia F7 | 2016/09/13 08:00 | Maciej Rajski v Mircea-Alexandru Jecan | 6-3,6-0 |
| ITF Italy F27 | 2016/08/30 14:55 | Luca Prevosto v Maciej Rajski | 6-2,7-6 |
| ITF Italy F27 | 2016/08/28 09:30 | Maciej Rajski v Francesco Bessire | 6-7,6-3,6-2 |
| ITF Poland F6 | 2016/08/24 09:00 | Orlando Luz v Maciej Rajski | 6-4,7-5 |
| ITF Poland F6 | 2016/08/22 12:00 | Maciej Rajski v Pawel Juszczak | 6-1,6-2 |
| ITF Poland F5 | 2016/08/16 10:20 | Maximilian Neuchrist v Maciej Rajski | 6-2,6-3 |
| ITF Serbia F7 Qual | 2016/09/10 07:00 | Aljaz Jakob Kaplja v Petar Pjevcevic | 5-7,6-1,4-6 |
| ITF Serbia F6 | 2016/09/08 09:20 | Aljaz Jakob Kaplja v Tomislav Jotovski | 3-6,3-6 |
| ITF Serbia F6 | 2016/09/07 10:05 | Nebojsa Milenkovic v Aljaz Jakob Kaplja | 6-1,6-7,0-6 |
| ITF Austria F6 | 2016/08/13 09:30 | Lukas Koncilia v Aljaz Jakob Kaplja | 6-1,7-6 |
| ITF Austria F4 Qual | 2016/07/23 07:00 | Nazar Khrustalev v Aljaz Jakob Kaplja | 4-6,5-7 |
| ITF Germany F8 Qual | 2016/07/17 08:30 | Karlo Cubelic v Aljaz Jakob Kaplja | 6-3,7-5 |
| ITF Bosnia and Herzegovina F2 Qual | 2016/05/15 08:00 | Aljaz Jakob Kaplja v Daniel Orlita | 7-6,1-6,2-6 |
| ITF Greece F5 | 2016/04/16 11:30 | Aljaz Jakob Kaplja v George Davies | 5-7,0-6 |