| Tournament details | |
|---|---|
| Country |  Slovenia | 
| Teams | 32 | 
| Final positions | |
| Champions | Olimpija (3rd title) | 
| Runner-up | Korotan Prevalje | 
| Tournament statistics | |
| Matches played | 38 | 
The 1999–2000 Slovenian Football Cup was the ninth season of the Slovenian Football Cup, Slovenia's football knockout competition.
Qualified clubs
| 1998–99 Slovenian PrvaLiga members | Qualified through MNZ Regional Cups
 
 | 
First round
| Team 1 | Score | Team 2 | 
|---|---|---|
| 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 (a.e.t.) (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 | 3–1 | Šmartno | 
| Idrija | 0–1 | Odranci | 
| Koper | 4–1 | Šentjur | 
| Ivančna Gorica | 0–1 | Korotan Prevalje | 
Round of 16
| 31 August 1999 | Črenšovci | 0–8 | Maribor | Črenšovci | 
| Report | Stadium: Črenšovci Sports Park Attendance: 1,000 Referee: Peter Šart | 
| 22 September 1999 | Koper | 0–3 | Gorica | Koper | 
| Report | Stadium: Bonifika Stadium Attendance: 500 Referee: Milan Mitrovič | 
| 22 September 1999 | Domžale | 0–2 | Primorje | Domžale | 
| Report | 
 | Stadium: Domžale Sports Park Attendance: 100 Referee: Matjaž Bohinc | 
| 22 September 1999 | Veržej | 0–8 | Korotan Prevalje | Veržej | 
| Report | 
 | Stadium: Veržej Sports Park Attendance: 100 Referee: Srečko Kandare | 
| 22 September 1999 | Olimpija Ljubljana | 5–1 | Pohorje | Ljubljana | 
| Report | 
 | Stadium: Bežigrad Stadium Attendance: 100 Referee: Robert Zirnstein | 
| 22 September 1999 | Britof | 0–6 | Celje | Britof | 
| Report | 
 | Stadium: Britof Stadium Attendance: 300 Referee: Bojan Brence | 
Quarter-finals
Olimpija won 6–2 on aggregate.
| Primorje | 0–2 | Korotan Prevalje | 
|---|---|---|
| Report | 
 | 
| Korotan Prevalje | 1–0 | Primorje | 
|---|---|---|
| 
 | Report | 
Korotan won 3–0 on aggregate.
Gorica won 5–4 on aggregate.
| Maribor | 3–2 | Celje | 
|---|---|---|
| Report | 
 | 
Maribor won 5–2 on aggregate.
Semi-finals
| Maribor | 3–1 | Korotan Prevalje | 
|---|---|---|
| 
 | Report | 
 | 
| Korotan Prevalje | 3–0 | Maribor | 
|---|---|---|
| 
 | Report | 
Korotan Prevalje won 4–3 on aggregate.
Olimpija won 3–2 on aggregate.
Final
| Korotan Prevalje | 2–1 | Olimpija | 
|---|---|---|
| 
 | Report | 
 | 
| Olimpija | 2–0 | Korotan Prevalje | 
|---|---|---|
| 
 | Report | 
Olimpija won 3–2 on aggregate.
References
- "Pokal Slovenije 1999/2000". Football Association of Slovenia official website. Archived from the original on 3 March 2001. Retrieved 10 April 2020.
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