1998–99 Slovenian Football Cup
| Country |
 Slovenia | ||
|---|---|---|---|
| Champions |
Maribor (4th title) | ||
| Runners-up | Olimpija | ||
| Matches played | 38 | ||
| |||
First round
| Home team | Score | Away team |
|---|---|---|
| Šmartno | 2–0 | Korotan Prevalje |
| Rogoza | 2–4 | Beltinci |
| Vevče | 0–1 | Olimpija |
| Jadran Hrpelje-Kozina | 0–3 | Maribor |
| Pobrežje | 0–4 | Primorje |
| Kolpa | 3–4 | Rudar Velenje |
| Ivančna Gorica | 0–2 | Triglav Kranj |
| Celje | 1–0 | Domžale |
| Ižakovci | 0–6 | Nafta Lendava |
| Aluminij | 2–0 | Brda |
| Tabor Sežana | 6–0 | Turnišče |
| Zarica Kranj | 1–3 | Goriške Opekarne |
| Drava Ptuj | 0–1 | Paloma |
| Goričanka | 3–0 | Dornava |
| Gorica | 2–3 | Mura |
| Veržej | 5–3 | Šoštanj |
Round of 16
| Home team | Score | Away team |
|---|---|---|
| Tabor Sežana | 1–2 | Maribor |
| Goričanka | 0–6 | Olimpija |
| Goriške Opekarne | 1–0 | Celje |
| Triglav Kranj | 1–2 | Rudar Velenje |
| Mura | 5–2 | Beltinci |
| Veržej | 0–7 | Paloma |
| Aluminij | 0–2 | Nafta Lendava |
| Šmartno | 4–2 | Primorje |
Quarter-finals
| Team #1 | Agg. | Team #2 | 1st leg | 2nd leg |
|---|---|---|---|---|
| Nafta Lendava | 1–4 | Mura | 0–3 | 1–1 |
| Maribor | 3–2 | Rudar Velenje | 1–0 | 2–2 |
| Šmartno | 5–1 | Paloma | 3–0 | 2–1 |
| Goriške Opekarne | 1–8 | Olimpija | 1–2 | 0–6 |
Semi-finals
| Team #1 | Agg. | Team #2 | 1st leg | 2nd leg |
|---|---|---|---|---|
| Olimpija | 2–1 | Šmartno | 1–1 | 1–0 |
| Maribor | 5–2 | Mura | 3–1 | 2–1 |
Final
First leg
26 May 1999 |
| Olimpija | 2 – 3 | Maribor |
|---|---|---|
Pejkovič  47' (pen.)Čauševič 52' |
Report (Slovene) | Djuranovič 61' Bozgo 65' 83' |
Second leg
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