| Round | Date | Result | ||
|---|---|---|---|---|
| Round 1 | 23/08/1958 | Levski Sofia | 0:2 | CSKA Sofia |
| Round 2 | 30/08/1958 | Spartak 1918 Varna | 0:0 | Levski Sofia |
| Round 3 | 07/09/1958 | Levski Sofia | 3:0 | Spartak-S 94 Plovdiv |
| Round 4 | 13/09/1958 | Lokomotiv Sofia | 2:1 | Levski Sofia |
| Round 5 | 20/09/1958 | Levski Sofia | 2:0 | Minyor Pernik |
| Round 6 | 19/10/1958 | Spartak 1919 Pleven | 0:1 | Levski Sofia |
| Round 7 | 26/10/1958 | Slavia 1913 Sofia | 4:1 | Levski Sofia |
| Round 8 | 02/11/1958 | Levski Sofia | 1:0 | Cherno More Varna |
| Round 9 | 16/11/1958 | Botev Plovdiv | 1:0 | Levski Sofia |
| Round 10 | 02/11/1958 | Levski Sofia | 2:0 | Beroe Stara Zagora |
| Round 11 | 30/11/1958 | Dunav 2010 Ruse | 1:0 | Levski Sofia |
| Round 12 | 08/03/1959 | CSKA Sofia | 0:1 | Levski Sofia |
| Round 13 | 22/04/1959 | Levski Sofia | 0:0 | Spartak 1918 Varna |
| Round 14 | 22/03/1959 | Spartak-S 94 Plovdiv | 1:0 | Levski Sofia |
| Round 15 | 10/04/1959 | Levski Sofia | 1:0 | Lokomotiv Sofia |
| Round 16 | 12/04/1959 | Minyor Pernik | 0:0 | Levski Sofia |
| Round 17 | 18/04/1959 | Levski Sofia | 4:0 | Spartak 1919 Pleven |
| Round 18 | 26/04/1959 | Levski Sofia | 0:0 | Slavia 1913 Sofia |
| Round 19 | 29/04/1959 | Cherno More Varna | 2:1 | Levski Sofia |
| Round 20 | 16/05/1959 | Levski Sofia | 4:1 | Botev Plovdiv |
| Round 21 | 07/06/1959 | Beroe Stara Zagora | 1:0 | Levski Sofia |
| Round 22 | 14/06/1959 | Levski Sofia | 5:0 | Dunav 2010 Ruse |