| ITF Turkey F24 | 06/20 10:40 | 25 | Μάθιου Σ Ρόμιος v Kaloyan Dimitrov | 6-1,6-1 | |
| ITF Turkey F20 | 05/21 09:30 | 44 | Kaloyan Dimitrov v Ερικ Χόλτ Κροσμαν | 3-6,4-6 | |
| ITF Bulgaria F1 | 05/11 07:00 | 26 | Kaloyan Dimitrov v Γιάν Σαμπάνιν | 3-6,2-6 | |
| ITF Bulgaria F1 | 05/09 08:40 | 25 | Aaron Cortes Alcaraz v Kaloyan Dimitrov | Retired | |
| ITF Turkey F16 | 04/22 09:00 | 62 | Kaloyan Dimitrov v Ίσα Μαμετγκουλίγιεφ | 4-6,0-6 | |
| ITF Turkey F12 | 03/27 07:00 | 44 | Κόρεϊ Κίρσι v Kaloyan Dimitrov | 6-7,6-3,6-4 | |
| ITF Turkey F12 | 03/26 07:00 | 44 | Maxim Bulat v Kaloyan Dimitrov | 4-6,3-6 | |
| ITF Turkey F11 | 03/18 10:00 | 62 | Γιούρι Τζαβακιάν v Kaloyan Dimitrov | 6-1,6-0 | |
| ITF Serbia F1 Qual | 07/18 07:30 | 62 | Nebojsa Peric v Kaloyan Dimitrov | 6-0,6-2 |