The Bulgarian Cup 2008–09 was the seventieth 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.
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In this round entered 4 winners from the regional competitions as well as 3 teams from B PFG (second level) decided by random draw. There should have been 4 teams selected from B PFG, but since this year's league features only 31 team, 3 teams were chosen. The matches were played on October 15, 2008.
| Team 1 | Score | Team 2 |
|---|---|---|
| Slivnishki Geroy (III) | 3–0 | Akademik Sofia (II) |
| Brestnik 1948 (III) | 1–3 | Pirin Gotse Delchev (II) |
| Dorostol 2003 (III) | 1–2 (aet) | Chavdar Etropole (II) |
| Almus Bier (III) | bye |
Note: Roman numerals in brackets denote the league tier the clubs participate in during the 2008–09 season.
In this round entered winners from the previous round together with the remaining 28 teams from B PFG. The matches were played on October 29, 2008.
| Team 1 | Score | Team 2 |
|---|---|---|
| Etar-1924 | 1–3 | Pirin Blagoevgrad (1922) |
| Belite orli | 0–2 | Balkan Botevgrad |
| Slivnishki Geroy | 2–2 (aet, p. 2–4) | Pirin Gotse Delchev |
| Botev Krivodol | 1–0 | Beroe |
| Marek | 0–0 (aet, p. 4–5) | Minyor |
| Almus Bier | 0–3 | Vidima-Rakovski |
| Spartak Plovdiv | 1–0 | Dunav Rousse |
| Chavdar Etropole | 3–1 | Kom-Minyor |
| Sportist Svoge | 1–0 | Lokomotiv Stara Zagora |
| Svetkavitsa | 1–1 (aet, p. 4–5) | Montana |
| Lyubimetz 2007 | 2–1 (aet) | Svilengrad 1921 |
| Spartak Pleven | 0–2 | Chernomorets Balchik |
| Nesebar | 2–1 (aet) | Naftex |
| Chavdar | 2–0 | Rilski Sportist |
| Maritsa | 2–1 | Shumen |
| Rodopa Smolyan | 2–1 | Kaliakra Kavarna |
This round featured winners from the First Round and all 16 teams from A PFG. The matches were played on November 11, 12, 13 and 26, 2008.
| Team 1 | Score | Team 2 |
|---|---|---|
| Lyubimetz 2007 | 1–2 | Vihren Sandanski |
| Lokomotiv Sofia | 1–2 (aet) | Levski Sofia |
| Balkan Botevgrad | 1–0 | Lokomotiv Mezdra |
| Minyor Pernik | 2–1 (aet) | Cherno More Varna |
| Spartak Varna | 1–2 | Pirin Blagoevgrad (1931) |
| Vidima-Rakovski | 1–0 | Chavdar Etropole |
| Litex Lovech | 2–0 | Botev Plovdiv |
| CSKA Sofia | 2–1 (aet) | Lokomotiv Plovdiv |
| Chavdar | 1–2 | Spartak Plovdiv |
| Pirin Gotse Delchev | 3–0 | Belasitsa Petrich |
| Maritsa | 2–0 | Sportist Svoge |
| Nesebar | 1–0 (aet) | Chernomorets Balchik |
| Minyor | 0–2 | OFC Sliven |
| Botev Krivodol | 2–1 | Slavia Sofia |
| Rodopa Smolyan | 2–1 (aet) | Chernomorets Burgas |
| Montana | 2–0 (aet) | Pirin Blagoevgrad (1922) |
In this round entered winners from the Second Round. The matches were played on December 7, 2008.
| Team 1 | Score | Team 2 |
|---|---|---|
| Montana | 0–2 | Pirin Blagoevgrad (1931) |
| Spartak Plovdiv | 2–3 | Vihren Sandanski |
| Maritsa | 1–5 | Litex Lovech |
| Balkan Botevgrad | 0–5 | CSKA Sofia |
| Vidima-Rakovski | 0–3 | Minyor Pernik |
| Rodopa Smolyan | 1–3 | Botev Krivodol |
| Nesebar | 2–1 | Pirin Gotse Delchev |
| Levski Sofia | 2–1 (aet) | OFC Sliven |
| March 4, 2009 14:00 EET |
Vihren Sandanski | 0 – 2 | Levski Sofia | Osogovo Kjustendil |
|---|---|---|---|---|
| G. Ivanov 12' Tasevski 28' |
| March 4, 2009 14:30 EET |
Botev Krivodol | 1 – 4 | Minyor Pernik | Ogosta Stadium, Montana |
|---|---|---|---|---|
| Vladinov 87' | Hazurov 17' 33' Janković 63' Rumenov 78' |
| March 4, 2009 14:30 EET |
Nesebar | 1 – 5 | Litex Lovech | Gradski Stadion, Nesebar |
|---|---|---|---|---|
| Hristov 15' | Popov 28' 71' Doka 60' Bibishkov 75' Cvetanov 77' |
| March 4, 2009 16:00 EET |
CSKA Sofia | 1 – 1 (aet) | Pirin Blagoevgrad (1931) | Balgarska Armiya Stadium, Sofia |
|---|---|---|---|---|
| Marquinhos 58' | Delev 70' | |||
| Penalties | ||||
| Todorov Saidhodzha Toshev Marquinhos |
3 – 5 | Nakov Hazurov Peev Palankov Galchev |
| April 29, 2009 14:00 EEST |
Minyor Pernik | 0 – 1 | Litex Lovech | Minyor Stadium, Pernik Attendance: 5,000 Referee: Stanislav Todorov |
|---|---|---|---|---|
| Bibishkov 57' |
| April 29, 2009 16:30 EEST |
Pirin Blagoevgrad (1931) | 1 – 0 | Levski Sofia | Hristo Botev Stadium, Blagoevgrad Attendance: 6,000 Referee: Georgi Ignatov |
|---|---|---|---|---|
| Peev 56' |
| May 26, 2009 20:30 EEST |
Pirin Blagoevgrad | 0 – 3 | Litex Lovech | Georgi Asparuhov Stadium, Sofia Attendance: 10,000 Referee: Stefan Spasov |
|---|---|---|---|---|
| Niflore 20' Doka 72' Bibishkov 86' |
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