| Europe Friendlies | 2019/07/27 15:00 | Borislav 2009 v FK Haskovo | L | 1-0 |
| Bulgaria Third League | 2019/06/06 15:00 | Rodopa v FK Haskovo | L | 1-0 |
| Bulgaria Third League | 2019/06/02 15:00 | FK Haskovo v FK Sozopol | L | 0-2 |
| Bulgaria Third League | 2019/05/08 15:00 | FK Haskovo v Sokol Markovo | W | 2-0 |
| Bulgaria Third League | 2019/05/04 15:00 | Chernomorets Burgas v FK Haskovo | L | 5-1 |
| Bulgaria Third League | 2019/04/21 14:00 | Levski Karlovo v FK Haskovo | W | 0-2 |
| Bulgaria Third League | 2019/04/14 14:00 | FK Haskovo v Neftochimik 1962 | L | 0-3 |
| Bulgaria Third League | 2019/03/27 13:00 | FK Gigant Saedinie v FK Haskovo | D | 1-1 |
| Bulgaria Third League | 2019/05/31 15:00 | Neftochimik 1962 v Svilengrad 1921 | L | 5-1 |
| Bulgaria Third League | 2019/05/18 15:00 | FC Sadovo v Svilengrad 1921 | L | 2-0 |
| Bulgaria Third League | 2019/05/08 15:00 | Asenovets v Svilengrad 1921 | D | 3-3 |
| Club Friendly List | 2019/01/19 11:00 | Svilengrad 1921 v CSKA 1948 Sofia | L | 0-4 |
| Bulgaria Third League | 2018/11/21 12:30 | Zagorets v Svilengrad 1921 | L | 3-2 |
| Bulgaria Third League | 2018/10/12 12:00 | Maritsa Plovdiv v Svilengrad 1921 | L | 2-0 |
| Bulgaria Amateur Cup | 2018/10/02 13:00 | FK Dimitrovgrad v Svilengrad 1921 | L | 1-0 |
| Bulgaria Third League | 2018/08/12 15:00 | Levski Karlovo v Svilengrad 1921 | D | 0-0 |