The 2008–09 Bulgarian Cup was the 27th official Bulgarian annual football tournament. The competition started on October 15, 2008 with the preliminary round and ended on May 26, 2009. The defending champions were Litex Lovech, who successfully defended their title against Pirin Blagoevgrad.

Preliminary round

In this round entered 4 winners from the regional competitions as well as 3 teams from B Group (second level) decided by random draw. There should have been 4 teams selected from B Group, but since this year's league features only 31 team, 3 teams were chosen. The matches were played on 15 October 2008. !colspan=3 style="background-color:#D0F0C0;" |15 October 2008 Note: Roman numerals in brackets denote the league tier the clubs participate in during the 2008–09 season.

First round

In this round entered winners from the previous round together with the remaining 28 teams from B Group. The matches were played on 29 October 2008. !colspan=3 style="background-color:#D0F0C0;" |29 October 2008

Second round

This round featured winners from the first round and all 16 teams from A Group. The matches were played on 11, 12, 13 and 26 November 2008. !colspan=3 style="background-color:#D0F0C0;" |11 November 2008 !colspan=3 style="background-color:#D0F0C0;" |12 November 2008 !colspan=3 style="background-color:#D0F0C0;" |13 November 2008 !colspan=3 style="background-color:#D0F0C0;" |26 November 2008 !colspan=3 style="background-color:#D0F0C0;" |3 December 2008

Third round

In this round entered winners from the second round. The matches were played on 7 December 2008. !colspan=3 style="background-color:#D0F0C0;" |7 December 2008

Quarter-finals

Semi-finals

Final