| Round | Date | Result | ||
|---|---|---|---|---|
| Round 1 | 06/08/1999 | Levski Sofia | 2:0 | Chernomorets 1919 Burgas |
| Round 2 | 15/08/1999 | Shumen 2010 | 1:4 | Levski Sofia |
| Round 3 | 21/08/1999 | Levski Sofia | 5:0 | Spartak 1918 Varna |
| Round 4 | 29/08/1999 | Levski Sofia | 3:0 | Lokomotiv Sofia |
| Round 5 | 11/09/1999 | Beroe Stara Zagora | 0:1 | Levski Sofia |
| Round 6 | 19/09/1999 | Levski Sofia | 6:0 | Belasitsa Petrich |
| Round 7 | 24/09/1999 | Litex Lovech | 1:1 | Levski Sofia |
| Round 8 | 03/10/1999 | Levski Sofia | 2:0 | Neftochimic 1962 Burgas |
| Round 9 | 15/11/1999 | Velbazhd Kyustendil | 1:3 | Levski Sofia |
| Round 10 | 24/10/1999 | Levski Sofia | 4:1 | Minyor Pernik |
| Round 11 | 31/10/1999 | CSKA Sofia | 1:0 | Levski Sofia |
| Round 12 | 07/11/1999 | Levski Sofia | 4:1 | Slavia 1913 Sofia |
| Round 13 | 20/11/1999 | Dobrudzha 1919 Dobrich | 0:1 | Levski Sofia |
| Round 14 | 28/11/1999 | Levski Sofia | 4:1 | Botev Plovdiv |
| Round 15 | 04/12/1999 | Pirin Blagoevgrad | 0:1 | Levski Sofia |
| Round 16 | 26/02/2000 | Chernomorets 1919 Burgas | 2:3 | Levski Sofia |
| Round 17 | 05/03/2000 | Levski Sofia | 3:0 | Shumen 2010 |
| Round 18 | 12/03/2000 | Spartak 1918 Varna | 0:1 | Levski Sofia |
| Round 19 | 17/03/2000 | Lokomotiv Sofia | 1:1 | Levski Sofia |
| Round 20 | 25/03/2000 | Levski Sofia | 2:0 | Beroe Stara Zagora |
| Round 21 | 31/03/2000 | Belasitsa Petrich | 0:0 | Levski Sofia |
| Round 22 | 08/04/2000 | Levski Sofia | 1:1 | Litex Lovech |
| Round 23 | 22/04/2000 | Neftochimic 1962 Burgas | 1:1 | Levski Sofia |
| Round 24 | 29/04/2000 | Levski Sofia | 3:0 | Velbazhd Kyustendil |
| Round 25 | 06/05/2000 | Minyor Pernik | 3:2 | Levski Sofia |
| Round 26 | 13/05/2000 | Levski Sofia | 1:0 | CSKA Sofia |
| Round 27 | 21/05/2000 | Slavia 1913 Sofia | 0:2 | Levski Sofia |
| Round 28 | 27/05/2000 | Levski Sofia | 2:1 | Dobrudzha 1919 Dobrich |
| Round 29 | 03/06/2000 | Botev Plovdiv | 1:2 | Levski Sofia |
| Round 30 | 09/06/2000 | Levski Sofia | 1:0 | Pirin Blagoevgrad |