1999–2000 Slovenian Football Cup
| Country |
 Slovenia | ||
|---|---|---|---|
| Champions |
Olimpija (3rd title) | ||
| Runners-up | Korotan Prevalje | ||
| Matches played | 38 | ||
| |||
First round
| Home team | Score | Away team |
|---|---|---|
| Drava Ptuj | 1–4 | Primorje |
| Triglav Kranj | 0–4 | Maribor |
| Brda | 0–2 | Celje |
| Tabor Sežana | 0–1 | Pohorje |
| Ilirska Bistrica | 0–2 | Domžale |
| Železničar Maribor | 1–1 (4–3) p. |
Beltinci |
| Aluminij | 0–2 | Olimpija |
| Mura | 2–0 | Rudar Velenje |
| Tromejnik | 0–9 | Gorica |
| Britof | 2–1 | Factor |
| Črenšovci | 5–0 | Paloma |
| Veržej | 3–0 (w.o.) | Lesce |
| Elan Novo Mesto | 3–1 | Šmartno |
| Idrija | 0–1 | Odranci |
| Koper | 4–1 | Šentjur |
| Ivančna Gorica | 0–1 | Korotan Prevalje |
Round of 16
| Home team | Score | Away team |
|---|---|---|
| Koper | 0–3 | Gorica |
| Domžale | 0–2 | Primorje |
| Železničar Maribor | 2–3 | Mura |
| Črenšovci | 0–8 | Maribor |
| Veržej | 0–8 | Korotan Prevalje |
| Olimpija | 5–1 | Pohorje |
| Britof | 0–6 | Celje |
| Elan Novo Mesto | 2–0 | Odranci |
Quarter-finals
| Team #1 | Agg. | Team #2 | 1st leg | 2nd leg |
|---|---|---|---|---|
| Celje | 2–5 | Maribor | 0–2 | 2–3 |
| Gorica | 5–4 | Elan Novo Mesto | 5–2 | 0–2 |
| Primorje | 0–3 | Korotan Prevalje | 0–2 | 0–1 |
| Mura | 2–6 | Olimpija | 1–2 | 1–4 |
Semi-finals
| Team #1 | Agg. | Team #2 | 1st leg | 2nd leg |
|---|---|---|---|---|
| Maribor | 3–4 | Korotan Prevalje | 3–1 | 0–3 |
| Olimpija | 3–2 | Gorica | 2–1 | 1–1 |
Final
First leg
Second leg
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