Home History
| Bulgaria Third League | 2022/05/01 14:00 | Sayana Haskovo v Asenovets | W | 3-1 |
| Bulgaria Third League | 2022/04/21 14:00 | Sokol Markovo v Sayana Haskovo | W | 1-3 |
| Bulgaria Third League | 2022/04/17 14:00 | Sayana Haskovo v Levski Karlovo | W | 2-0 |
| Bulgaria Amateur Cup | 2022/03/30 14:00 | Sayana Haskovo v Rozova Dolina | W | 2-1 |
| Bulgaria Amateur Cup | 2022/03/23 13:00 | FK Gigant Saedinie v Sayana Haskovo | W | 0-1 |
| Bulgaria Third League | 2022/03/13 13:00 | Sayana Haskovo v Yambol 1915 | W | 3-0 |
| Bulgaria Third League | 2022/02/20 12:00 | Sayana Haskovo v Beroe Stara Zagora II | W | 6-0 |
| Bulgaria Third League | 2021/11/19 12:30 | Atletik Kuklen v Sayana Haskovo | D | 0-0 |
Away History
| Bulgaria Third League | 2021/10/23 12:00 | FK Dimitrovgrad v Borislav 2009 | W | 2-1 |
| Bulgaria Third League | 2021/09/05 14:00 | FK Dimitrovgrad v Asenovets | W | 3-1 |
| Bulgaria Third League | 2021/05/12 15:00 | FK Haskovo v FK Dimitrovgrad | L | 2-0 |
| Bulgaria Third League | 2021/04/29 14:00 | Borislav 2009 v FK Dimitrovgrad | L | 2-1 |
| Bulgaria Third League | 2021/04/21 14:00 | Zagorets v FK Dimitrovgrad | L | 2-1 |
| Bulgaria Third League | 2021/04/14 14:00 | Levski Karlovo v FK Dimitrovgrad | L | 2-0 |
| Bulgaria Third League | 2021/02/20 12:00 | Sokol Markovo v FK Dimitrovgrad | D | 1-1 |
| Bulgaria Third League | 2020/10/17 13:00 | Vereya v FK Dimitrovgrad | W | 1-2 |