| Croatian Football Cup | |
| Year: | 1998–99 |
| Country: | Croatia |
| Num Teams: | 48 |
| Defending Champions: | Croatia Zagreb |
| Winners: | Osijek (1st title) |
| Second: | Cibalia |
| Scoring Leader: | Željko Pakasin (5) |
| Prev Season: | 1997–98 |
| Next Season: | 1999–2000 |
The 1998–99 Croatian Football Cup was the eighth edition of Croatia's football knockout competition. Croatia Zagreb were the defending champions, and it was won by Osijek. This was the first season when a preliminary round was played, with top-level clubs entering the competition in the first round proper.
| Round | Main date | Number of fixtures | width=100 | Clubs ! | New entries this round |
|---|---|---|---|---|---|
| 19 August 1998 | 16 | 48 → 32 | none | ||
| 6 and 15 September 1998 | 16 | 32 → 16 | 16 | ||
| 23 and 29 September 1998 | 8 | 16 → 8 | none | ||
| 28 October and 25 November 1998 | 8 | 8 → 4 | none | ||
| 3 March and 17 March 1999 | 4 | 4 → 2 | none | ||
| 30 May 1999 | 2 | 2 → 1 | none | ||
| width=40 | Tie no | width=150 | Home team | width=80 | Score | width=150 | Away team |
|---|---|---|---|---|---|---|---|
| 1 | Mosor | 11–0 | Daruvar | ||||
| 2 | Valpovka | 1–2 | Samobor | ||||
| 3 | Čakovec | 3–0 | Croatia Đakovo | ||||
| 4 | Slavonija Požega | 5–0 | Spartak Vest | ||||
| 5 | Dugo Selo | 2–1 | Posavina Zagreb | ||||
| 6 | Halubjan Viškovo | 3–0 | Dugopolje | ||||
| 7 | Podravac | 2–1 | Slunj | ||||
| 8 | Ivančica | 1–4 | Slaven Belupo | ||||
| 9 | Bojovnik 7 | 1–0 | Slavonac | ||||
| 10 | Pazinka | 1–0 | Varaždin | ||||
| 11 | Zagora Unešić | 0–2 | Moslavina | ||||
| 12 | Amater Slavonski Brod | 6–1 | Mladost Hrastovec | ||||
| 13 | Istra Pula | 3–2 | Graničar Županja | ||||
| 14 | Raštane | 2–0 | Nehaj Senj | ||||
| 15 | TŠK Topolovac | 4–0 | Neretva | ||||
| 16 | Špansko | 0–1 | Mladost 127 |
| width=40 | Tie no | width=150 | Home team | width=80 | Score | width=150 | Away team |
|---|---|---|---|---|---|---|---|
| 1 | Dugo Selo | 3–2 | Croatia Zagreb | ||||
| 2 | Bojovnik 7 | 2–3 | Hajduk Split | ||||
| 3 | TŠK Topolovac | 0–1 | Varteks | ||||
| 4 | Amater Slavonski Brod | 2–2 (4–2 p) | NK Zagreb | ||||
| 5 | Halubjan | 1–2 | Rijeka | ||||
| 6 | Mosor | 0–1 (aet) | Osijek | ||||
| 7 | Podravac | 1–5 | Zadarkomerc | ||||
| 8 | Moslavina | 2–3 | Segesta | ||||
| 9 | Raštane | 2–0 | Inker Zaprešić | ||||
| 10 | Čakovec | 2–0 | Dubrovnik | ||||
| 11 | Samobor | 1–2 | Hrvatski Dragovoljac | ||||
| 12 | Pazinka | 0–6 | Cibalia | ||||
| 13 | Slavonija Požega | 0–3 | Belišće | ||||
| 14 | Istra Pula | 1–1 (1–4 p) | Šibenik | ||||
| 15 | Mladost 127 | 4–2 | Bjelovar | ||||
| 16 | Marsonia | 0–4 | Slaven Belupo |
| width=40 | Tie no | width=150 | Home team | width=80 | Score | width=150 | Away team |
|---|---|---|---|---|---|---|---|
| 1 | Slaven Belupo | 8–0 | Dugo Selo | ||||
| 2 | Hajduk Split | 5–1 | Mladost 127 | ||||
| 3 | Šibenik | 0–1 | Varteks | ||||
| 4 | Belišće | 4–1 | Amater Slavonski Brod | ||||
| 5 | Cibalia | 1–0 | Rijeka | ||||
| 6 | Osijek | 3–1 | Hrvatski Dragovoljac | ||||
| 7 | Čakovec | 0–0 (5–4 p) | Zadarkomerc | ||||
| 8 | Segesta | 4–0 | Raštane |
|}
3–3 on aggregate. Cibalia won 6–5 in penalty shootout.----Osijek won 1–0 on aggregate.
See main article: 1999 Croatian Football Cup final.