| Round | Date | Result | ||
|---|---|---|---|---|
| 16th-finals | 26/11/2008 | Lokomotiv Sofia | 1:2 | Levski Sofia |
| 8th-finals | 06/12/2008 | Levski Sofia | 2:1 | Sliven 2000 |
| Quarter-finals | 04/03/2009 | Vihren Sandanski | 0:2 | Levski Sofia |
| Semi-finals | 29/04/2009 | Pirin-Blagoevgrad Blagoevgrad | 1:0 | Levski Sofia |