Stadium: Court 5 Round: 25 Ground: Clay
| Challenger Bangkok 1A | 2019/02/21 03:00 | Dimitar Kuzmanov v James Duckworth | 3-6,1-6 |
| Challenger Bangkok | 2019/02/13 03:00 | Yuichi Sugita v Dimitar Kuzmanov | 6-4,6-4 |
| Challenger Bangkok | 2019/02/12 03:00 | Evgeny Tyurnev v Dimitar Kuzmanov | 3-6,1-6 |
| ATP Sofia | 2019/02/05 16:00 | Robin Haase v Dimitar Kuzmanov | 6-2,6-4 |
| Challenger Rennes | 2019/01/21 18:40 | Manuel Guinard v Dimitar Kuzmanov | 3-6,6-3,6-4 |
| ITF M15 Bressuire | 2019/01/16 10:00 | Dimitar Kuzmanov v Artem Dubrivnyy | 6-7,6-7 |
| Challenger Buenos Aires | 2018/11/17 20:40 | Dimitar Kuzmanov v Pedro Cachin | 3-6,6-7 |
| Challenger Buenos Aires | 2018/11/16 19:00 | Bastian Malla v Dimitar Kuzmanov | 4-6,2-6 |
| ITF M15 Antalya | 2019/02/14 09:45 | Tadeas Paroulek v Bogdan Ionut Apostol | 6-1,6-3 |
| ITF M15 Antalya | 2019/02/12 07:00 | Bogdan Ionut Apostol v Conner Huertas Del Pino | 6-2,6-4 |
| ITF M15 Antalya | 2019/02/11 07:00 | Bogdan Ionut Apostol v Pavle Daljev | 6-2,6-7,10-3 |
| ITF M15 Antalya | 2019/02/08 09:40 | Dejan Katic v Bogdan Ionut Apostol | 6-4,6-2 |
| ITF M15 Antalya | 2019/02/05 08:30 | Markos Kalovelonis v Bogdan Ionut Apostol | 1-6,3-6 |
| ITF M15 Antalya | 2019/02/03 07:00 | Kirill Kivattsev v Bogdan Ionut Apostol | 7-6,7-6 |
| ITF M15 Antalya | 2019/02/02 10:30 | Bogdan Ionut Apostol v Juan Manuel Cerundolo | 6-3,6-3 |
| ITF M15 Antalya | 2019/02/01 09:00 | Bogdan Ionut Apostol v Ivan Sabanov | 6-2,2-6,10-5 |