| Round | Date | Result | ||
|---|---|---|---|---|
| 16th-finals | 27/10/1999 | Iskar Sofia | 2:4 | Levski Sofia |
| 8th-finals | 10/11/1999 | Levski Sofia | 2:0 | Litex Lovech |
| 08/12/1999 | Litex Lovech | 3:1 | Levski Sofia | |
| Quarter-finals | 22/03/2000 | CSKA Sofia | 0:1 | Levski Sofia |
| 05/04/2000 | Levski Sofia | 3:1 | CSKA Sofia | |
| Semi-finals | 18/04/2000 | Levski Sofia | 6:1 | Velbazhd Kyustendil |
| 03/05/2000 | Velbazhd Kyustendil | 1:0 | Levski Sofia | |
| Final | 31/05/2000 | Neftochimic 1962 Burgas | 0:2 | Levski Sofia |