1999–2000 Croatian Football Cup
The 1999–2000 Croatian Football Cup was the ninth edition of Croatia's football knockout competition. The first match was played on 4 August 1999 and five rounds were played before the final, which took place over two legs on 2 and 16 May 2000.
Defending champions Osijek reached the competition's quarter finals, but lost to eventual semi-finalists Cibalia.
In the final Hajduk Split beat NK Zagreb over two matches, winning 2–0 at home before losing 1–0 away in the return fixture, therefore winning 2–1 on aggregate.
Preliminary round
The preliminary round was played between 4 and 14 August 1999. The round's highest scoring fixture was the 7–0 home win for Čazmatrans at the expense of Podravac Virje.| Tie no | Home team | Score | Away team |
| 1 | RNK Split | 3–2 | TŠK Topolovac |
| 2 | Koprivnica | 3–1 | Valpovka |
| 3 | Pomorac Kostrena | 1–1 | Marsonia |
| 4 | Čazmatrans | 7–0 | Podravac Virje |
| 5 | Mosor | 2–0 | Čakovec |
| 6 | Špansko | 4–1 | Olimpija Osijek |
| 7 | Duga Resa | 0–1 | Omladinac Novo Selo Rok |
| 8 | Zagorec Krapina | 4–1 | Dinara Knin |
| 9 | Pazinka | 1–2 | Neretva |
| 10 | Amater Slavonski Brod | 1–4 | Vukovar '91 |
| 11 | Moslavac Popovača | 2–1 | Dubrava |
| 12 | BSK Buk | 5–0 | Hajduk Hercegovac |
| 13 | Mladost 127 | 0–1 | Uljanik Pula |
| 14 | Pakoštane | 2–4 | Nehaj Senj |
| 15 | Sloboda Varaždin | 3–0 | PIK Vrbovec |
| 16 | Ivančica Ivanec | 0–2 | Radnik Velika Gorica |
First round
The first round was played between 21 September and 6 October 1999. 32 teams were involved in this round. Croatia Zagreb had the biggest win in this round, defeating BSK Buk 10–0 away from home.| Tie no | Home team | Score | Away team |
| 1 | Bjelovar | 2–1 | Dubrovnik |
| 2 | Neretva | 2–1 | Inker Zaprešić |
| 3 | Moslavac Popovača | 0–8 | Hajduk Split |
| 4 | Koprivnica | 1–2 | Varteks |
| 5 | Uljanik Pula | 0–2 | NK Zagreb |
| 6 | Čazmatrans | 1–2 | Cibalia |
| 7 | Vukovar '91 | 0–1 | Slaven Belupo |
| 8 | Nehaj Senj | 2–2 | Zadarkomerc |
| 9 | Radnik Velika Gorica | 1–2 | Rijeka |
| 10 | Mosor | 0–0 | Segesta |
| 11 | Sloboda Varaždin | 1–2 | Hrvatski Dragovoljac |
| 12 | BSK Buk | 0–10 | Croatia Zagreb |
| 13 | Zagorec Krapina | 3–1 | Belišće |
| 14 | Špansko | 1–2 | Šibenik |
| 15 | RNK Split | 0–4 | Marsonia |
| 16 | Omladinac Novo Selo Rok | 2–3 | Osijek |
Second round
The second round was played between 26 October and 11 November 1999. 16 teams were involved in this round. NK Zagreb had the biggest win in this round, defeating Neretva 6–0 away from home.| Tie no | Home team | Score | Away team |
| 1 | Cibalia | 2–1 | Hrvatski Dragovoljac |
| 2 | Nehaj Senj | 0–1 | Rijeka |
| 3 | Neretva | 0–6 | NK Zagreb |
| 4 | Hajduk Split | 3–1 | Šibenik |
| 5 | Bjelovar | 1–3 | Osijek |
| 6 | Zagorec Krapina | 0–1 | Varteks |
| 7 | Mosor | 0–2 | Slaven Belupo |
| 8 | Croatia Zagreb | 4–0 | Marsonia |
Quarter-finals
The quarter finals were held on a home and away basis. First legs were held on 14 March 2000 and the return legs took place on 21 March 2000. All four of the ties were decided by a single goal.Semi-finals
The semi finals were held on a home and away basis. First legs were held on 4 April 2000 and the return legs took place two weeks later on 18 April 2000. Dinamo Zagreb scored six goals across the two matches, advancing past Cibalia, who scored a single goal. In the other semi final, Hajduk Split progressed against NK Zagreb, 4–3 on aggregate.Dinamo Zagreb won 6–1 on aggregate.
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''Hajduk Split won 4–3 on aggregate.''