Stadium: Court 6 Round: 45 Ground: Hardcourt outdoor
| ITF M15 Monastir | 2019/02/11 08:00 | Alexis Canter v Kristjan Tamm | 6-1,4-6,7-10 |
| ITF M15 Monastir | 2019/02/04 10:00 | Brian Bencic v Kristjan Tamm | 6-7,7-5,10-4 |
| ITF Tunisia F44 | 2018/12/10 08:30 | Yan Bondarevskiy v Kristjan Tamm | 6-3,6-1 |
| ITF Tunisia F44 | 2018/12/08 08:00 | Vitalii Shcherba v Kristjan Tamm | 0-6,3-6 |
| ITF Tunisia F43 | 2018/12/06 08:00 | Kristjan Tamm v Evan Hoyt | 3-6,2-6 |
| ITF Tunisia F43 | 2018/12/05 10:10 | Kristjan Tamm v Erik Crepaldi | 7-6,6-3 |
| ITF Tunisia F43 | 2018/12/03 08:30 | Maikel Borg v Kristjan Tamm | 5-7,3-6 |
| ITF Tunisia F43 | 2018/12/02 08:00 | Himansu Sagar v Kristjan Tamm | 4-6,0-6 |
| ITF M15 Monastir | 2019/02/11 08:00 | Ivan Marrero Curbelo v Vasko Mladenov | 0-6,3-6 |
| ITF Estonia F3 | 2018/11/06 09:00 | Julius Tverijonas v Vasko Mladenov | 6-4,6-4 |
| ITF Estonia F2 | 2018/10/30 08:00 | Aliaksandr Prudnikau v Vasko Mladenov | 6-4,6-3 |
| ITF Tunisia F33 | 2018/09/27 08:30 | Robert Strombachs v Vasko Mladenov | 6-4,6-7,6-2 |
| ITF Tunisia F33 | 2018/09/25 08:30 | Juan Ignacio Batalla v Vasko Mladenov | 2-6,4-6 |
| ITF Tunisia F32 | 2018/09/21 08:30 | Kai Wehnelt v Vasko Mladenov | 6-2,6-0 |
| ITF Tunisia F32 | 2018/09/20 10:30 | Amaury Delmas v Vasko Mladenov | 6-4,2-6,3-6 |
| ITF Tunisia F32 | 2018/09/19 11:25 | Vasko Mladenov v Luca Giacomini | 6-7,6-2,6-2 |