| Wimbledon | 06/23 10:00 | 19 | [175] Dimitar Kuzmanov v Enzo Couacaud [207] | 2-6,7-6,3-6,2-6 | |
| Wimbledon | 06/22 10:00 | 19 | [118] Pedro Cachin v Dimitar Kuzmanov [175] | 4-6,6-3,4-6 | |
| Wimbledon | 06/20 10:00 | 14 | [175] Dimitar Kuzmanov v Charles Broom [417] | 6-3,7-5 | |
| Challenger Poznan | 06/04 12:35 | 28 | [68] Arthur Rinderknech v Dimitar Kuzmanov [197] | 6-3,7-6 | |
| Challenger Poznan | 06/03 15:20 | 27 | [108] Chun Hsin Tseng v Dimitar Kuzmanov [197] | 4-6,2-6 | |
| Challenger Poznan | 06/02 10:00 | 26 | [198] Dimitar Kuzmanov v Hugo Grenier [151] | 6-2,6-1 | |
| Challenger Poznan | 05/31 08:00 | 25 | [308] Oleksii Krutykh v Dimitar Kuzmanov [198] | 2-6,5-7 | |
| French Open | 05/19 08:00 | 19 | [193] Dimitar Kuzmanov v Santiago F R Taverna [203] | 4-6,6-3,3-6 | |
| French Open | 05/18 08:00 | 15 | [193] Dimitar Kuzmanov v Flavio Cobolli [153] | 6-3,3-6,6-3 | |
| French Open | 05/16 10:25 | 14 | [120] Marc-Andrea Huesler v Dimitar Kuzmanov [193] | 5-7,3-6 | |
| Challenger Zagreb | 05/11 09:50 | 25 | [171] Vit Kopriva v Dimitar Kuzmanov [194] | 6-4,1-6,6-3 | |
| Challenger Prague | 05/07 09:00 | 28 | [223] Lorenzo Giustino v Dimitar Kuzmanov [206] | 7-6,4-6,6-2 |