| Round | Date | Result | ||
|---|---|---|---|---|
| Round 1 | 09/08/2008 | Vihren 1925 Sandanski | 1:0 | Levski Sofia |
| Round 2 | 17/08/2008 | Levski Sofia | 6:0 | Botev Plovdiv |
| Round 3 | 05/11/2008 | Chernomorets-Burgas Burgas | 2:2 | Levski Sofia |
| Round 4 | 31/08/2008 | Lokomotiv 1926 Plovdiv | 2:3 | Levski Sofia |
| Round 5 | 12/09/2008 | Levski Sofia | 3:0 | Cherno More Varna |
| Round 6 | 21/09/2008 | Lokomotiv Sofia | 1:0 | Levski Sofia |
| Round 7 | 27/09/2008 | Levski Sofia | 2:0 | Litex Lovech |
| Round 8 | 06/10/2008 | Lokomotiv Mezdra | 0:1 | Levski Sofia |
| Round 9 | 18/10/2008 | Levski Sofia | 2:0 | Belasitsa Petrich |
| Round 10 | 26/10/2008 | Sliven 2000 | 0:0 | Levski Sofia |
| Round 11 | 01/11/2008 | Levski Sofia | 1:1 | CSKA Sofia |
| Round 12 | 09/11/2008 | Spartak 1918 Varna | 0:1 | Levski Sofia |
| Round 13 | 16/11/2008 | Levski Sofia | 1:0 | Slavia 1913 Sofia |
| Round 14 | 23/11/2008 | Minyor Pernik | 0:2 | Levski Sofia |
| Round 15 | 29/11/2008 | Levski Sofia | 2:0 | Pirin-Blagoevgrad Blagoevgrad |
| Round 16 | 08/03/2009 | Levski Sofia | 3:2 | Vihren 1925 Sandanski |
| Round 17 | 14/03/2009 | Botev Plovdiv | 0:1 | Levski Sofia |
| Round 18 | 18/03/2009 | Levski Sofia | 3:1 | Chernomorets-Burgas Burgas |
| Round 19 | 22/03/2009 | Levski Sofia | 1:0 | Lokomotiv 1926 Plovdiv |
| Round 20 | 04/04/2009 | Cherno More Varna | 0:0 | Levski Sofia |
| Round 21 | 11/04/2009 | Levski Sofia | 0:3 | Lokomotiv Sofia |
| Round 22 | 17/04/2009 | Litex Lovech | 1:2 | Levski Sofia |
| Round 23 | 23/04/2009 | Levski Sofia | 3:1 | Lokomotiv Mezdra |
| Round 24 | 26/04/2009 | Belasitsa Petrich | 1:7 | Levski Sofia |
| Round 25 | 03/05/2009 | Levski Sofia | 1:0 | Sliven 2000 |
| Round 26 | 09/05/2009 | CSKA Sofia | 0:2 | Levski Sofia |
| Round 27 | 17/05/2009 | Levski Sofia | 5:0 | Spartak 1918 Varna |
| Round 28 | 23/05/2009 | Slavia 1913 Sofia | 0:1 | Levski Sofia |
| Round 29 | 31/05/2009 | Levski Sofia | 1:1 | Minyor Pernik |
| Round 30 | 13/06/2009 | Pirin-Blagoevgrad Blagoevgrad | 1:1 | Levski Sofia |