Round: 26 Ground: Clay
| ITF Bosnia and Herzegovina F2 | 2016/05/17 12:05 | Silva, Caio v Jotovski, Tomislav | 1-6,3-6 |
| ITF Bosnia and Herzegovina F1 | 2016/05/14 08:00 | Jotovski, Tomislav v Mesaros, Kristijan | 5-7,0-6 |
| ITF Bosnia and Herzegovina F1 | 2016/05/13 09:00 | David Pichler v Jotovski, Tomislav | 6-4,2-6,2-6 |
| ITF Bosnia and Herzegovina F1 | 2016/05/12 09:15 | Stosic, Marko v Jotovski, Tomislav | 4-6,3-6 |
| ITF Bosnia and Herzegovina F1 | 2016/05/11 12:35 | Conkic, Petar v Jotovski, Tomislav | 4-6,0-6 |
| ITF Hungary F3 | 2016/05/03 10:10 | Jotovski, Tomislav v Mate Valkusz | 5-7,6-7 |
| ITF Hungary F2 | 2016/04/26 08:00 | Antonescu, Vasile v Jotovski, Tomislav | 4-6,6-3,7-5 |
| ITF Hungary F1 | 2016/04/19 12:00 | Antonescu, Vasile v Jotovski, Tomislav | 6-1,6-4 |
| ITF Bosnia and Herzegovina F2 | 2016/05/17 08:00 | Kalenichenko, Danylo v Baluda, Victor | 6-3,6-7,7-6 |
| ITF Bosnia and Herzegovina F1 | 2016/05/14 08:00 | Kalenichenko, Danylo v Nino Serdarusic | 1-6,3-6 |
| ITF Bosnia and Herzegovina F1 | 2016/05/13 08:00 | Nerman Fatic v Kalenichenko, Danylo | 3-6,6-1,6-7 |
| ITF Bosnia and Herzegovina F1 | 2016/05/12 08:45 | Kalenichenko, Danylo v Wilson Leite | 6-3,6-2 |
| ITF Bosnia and Herzegovina F1 | 2016/05/11 09:30 | Silva, Caio v Kalenichenko, Danylo | 3-6,3-6 |
| ITF Italy F1 | 2016/03/02 12:30 | Kalenichenko, Danylo v Hugo Grenier | 6-4,1-6,4-6 |
| Challenger Wroclaw Qual | 2016/02/13 10:55 | Kalenichenko, Danylo v Vasilevski, Andrei | 7-6,6-7,6-7 |
| ITF Germany F3 Qual | 2016/01/24 11:00 | Majchrowicz, Adam v Kalenichenko, Danylo | 6-3,6-4 |