Stadium: Center Court Round: 25 Ground: Clay
| Challenger Amersfoort | 2019/07/20 14:10 | Blaz Rola v Kimmer Coppejans | 4-6,0-6 |
| Challenger Amersfoort | 2019/07/19 09:00 | Zdenek Kolar v Blaz Rola | 5-7,4-6 |
| Challenger Amersfoort | 2019/07/18 12:25 | Ignatik, Uladzimir v Blaz Rola | 4-6,6-4,0-6 |
| Challenger Amersfoort | 2019/07/16 12:45 | Pavlasek, Adam v Blaz Rola | 6-4,3-6,1-6 |
| Wimbledon, London, Great Britain | 2019/06/26 10:00 | Blaz Rola v Brands, Daniel | 7-6,6-7,5-7 |
| Wimbledon, London, Great Britain | 2019/06/24 14:10 | Stefano Travaglia v Blaz Rola | 7-6,2-6,4-6 |
| Challenger Bratislava | 2019/06/22 11:00 | Balazs, Attila v Blaz Rola | 6-2,3-6,6-3 |
| Challenger Bratislava | 2019/06/21 10:00 | Blaz Rola v Mohamed Safwat | 7-6,6-4 |
| Challenger Tampere | 2019/07/22 12:30 | Dimitar Kuzmanov v Andrea Pellegrino | 4-6,6-3,7-5 |
| Challenger Amersfoort | 2019/07/16 14:25 | Dimitar Kuzmanov v Kimmer Coppejans | 3-6,6-1,1-6 |
| Challenger Amersfoort | 2019/07/15 08:00 | Geoffrey Blancaneaux v Dimitar Kuzmanov | 5-7,1-6 |
| Cuneo, Singles Qualifying M-ITF-ITA-12A | 2019/07/05 10:30 | Gijs Brouwer v Dimitar Kuzmanov | 6-7,6-4,6-2 |
| Cuneo, Singles Qualifying M-ITF-ITA-12A | 2019/07/04 09:30 | Remy Bertola v Dimitar Kuzmanov | 2-6,0-6 |
| Milan, Italy | 2019/06/26 13:10 | Balzerani, Riccardo v Dimitar Kuzmanov | 2-6,6-2,6-3 |
| Milan, Italy | 2019/06/25 08:00 | Corentin Denolly v Dimitar Kuzmanov | 3-6,4-6 |
| Parma II, Italy | 2019/06/19 16:25 | Dimitar Kuzmanov v Stefano Travaglia | 5-7,4-6 |