2008–09 Bulgarian Cup

The 2008–09 Bulgarian Cup was the 27th season of the annual knockout football tournament for Bulgaria. The competition started on 15 October 2008 with the preliminary round and ended on 26 May 2009. The defending champions were Litex Lovech, who successfully defended their title against Pirin Blagoevgrad and resultantly qualified for the 2009–10 UEFA Europa League.

Preliminary round

Seven teams entered the preliminary round: four teams from the amateur level, plus three teams from the B Group. Six of the teams played against another opponent, while the seventh team, amateur side Almus Bier, received a bye to the first round of the cup. The matches were played on 15 October 2008. Of the professional teams, only Akademik Sofia lost, suffering a 3–0 defeat away to Slivnishki Geroy.
!colspan=3 style="background-color:#D0F0C0;" |'''15 October 2008'''

First round

The first round included the four teams advancing from the preliminary round as well as the remaining 28 teams from the B Group. The matches were played on 29 October 2008. Both amateur teams were eliminated in this round. In a close series of matches, five games went to extra time and in three cases the teams were separated after a penalty shootout.
!colspan=3 style="background-color:#D0F0C0;" |'''29 October 2008'''

Second round

The 16 teams from A Group entered in the second round, joining the 16 winners from the first round. The matches were played from 11 November to 3 December 2008. Six of the ties required extra time, but no penalty shootouts were required.
!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

The third round was played on 7 December 2008 and featured the 16 winners of round two. The biggest win of the third round was CSKA Sofia's 5–0 victory at Balkan Botevgrad.
!colspan=3 style="background-color:#D0F0C0;" |'''7 December 2008'''

Quarter-finals

The quarter-finals were held on 4 March 2009. All four away teams won their matches to advance to the semi-final stage.

Semi-finals

Both semi-finals were held on 29 April 2009. Litex Lovech beat Minyor Pernik, and Pirin Blagoevgrad (1931) defeated Levski Sofia, in each case by a single goal.

Final

Last season's winners Litex Lovech defended their title with a 3–0 win against Pirin Blagoevgrad (1931) at the Georgi Asparuhov Stadium in Sofia. By winning, Litex Lovech ensured they would enter in the third qualifying round of the following season's UEFA Europa League. The game was broadcast live on Bulgarian National Television.