The Slovenian Cup 2008–09 was the eighteenth season of Slovenia's football knockout competition. It started on August 2, 2008 with the First Round games and ended on May 30, 2009 with the Final. The defending champions were Interblock Ljubljana.
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In this round entered 19 teams from Slovenian second and third division. Since NK Izola withrew from the competition before the beginning, Adria Miren received a bye to the Second Round. The matches were played on August 2 and 19, 2008.
| Team 1 | Score | Team 2 |
|---|---|---|
| Zavrč | 3–0 (f) | Korotan Prevalje |
| Črenšovci | 2–5 | Aluminij Kidričevo |
| Šentjur | 8–1 | Polana |
| Mura 05 | 11–0 | Koroške Gradnje Slovenj Gradec |
| Dravograd | 9–1 | Roma |
| Bela Krajina | 1–2 | Bonifika Izola |
| Olimpija Ljubljana | 8–0 | Velesovo |
| Idrija | 1–2 | Krka Novo mesto |
| Šenčur | 3–2 | Krško |
In this round entered winners from the previous round as well as one team who had received a bye. The matches were played on September 3, 2008.
| Team 1 | Score | Team 2 |
|---|---|---|
| Krka Novo mesto | 3–0 | Aluminij Kidričevo |
| Mura 05 | 3–1 | Šentjur |
| Zavrč | 1–0 | Dravograd |
| Šenčur | 0–1 | Olimpija Ljubljana |
| Adria Miren | 1–5 | Bonifika Izola |
In this round entered winners from the previous round as well as all teams from Slovenian PrvaLiga. In the Third Round also entered NK Livar who got relegated to the second division at the end of the last year's PrvaLiga. The matches were played on September 16 and 17, 2008.
| Team 1 | Score | Team 2 |
|---|---|---|
| Mura 05 | 1–3 | Maribor |
| Krka Novo mesto | 1–3 | Nafta Lendava |
| Koper | 1–1 (aet, p. 3–1) | Olimpija Ljubljana |
| Rudar Velenje | 2–1 | Celje |
| Domžale | 1–4 | Livar |
| Bonifika Izola | 1–2 | Interblock Ljubljana |
| HIT Gorica | 2–1 | Drava Ptuj |
| Primorje | 5–0 | Zavrč |
The matches were played on October 22, 2008.
| Team 1 | Score | Team 2 |
|---|---|---|
| Primorje | 2–3 | Interblock Ljubljana |
| Maribor | 2–0 | Rudar Velenje |
| Koper | 1–1 (aet, p. 3–2) | Nafta Lendava |
| HIT Gorica | 6–0 | Livar |
The first legs were played on April 15, 2009. The second legs were played on April 29, 2009.
| Team 1 | Agg. | Team 2 | 1st leg | 2nd leg |
|---|---|---|---|---|
| HIT Gorica | 3–4 | Koper | 2–4 | 1–0 |
| Interblock Ljubljana | 5–4 | Maribor | 2–2 | 3–2 |
| May 30, 2009 20:00 |
Interblock Ljubljana | 2 – 1 | Koper | Ljudski vrt, Maribor Attendance: 2,500 Referee: Darko Čeferin |
|---|---|---|---|---|
| Berič 40' Rakovič 53' |
[1] | Viler 76' |
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