Preliminary
26/08/2008 15:30 NK Moslavina Kutina - NK Istra Tar 7:0
15:30 NK Međimurje - HNK Trogir 3:0
15:30 HNK Suhopolje - NK Križevci 5:4 pso
15:30 Hrvatski Dragovoljac - Granicar Tucenik 1:0
27/08/2008 15:30 NK Žminj - NK Gaj Mace 0:2
15:30 NK Croatia Đakovo - NK Polet Buševec 1:3
15:30 NK Bjelovar - NK Zagora Unešić 2:4
15:30 NK Orijent Rijeka - NK Raštane 1:0
15:30 NK Mladost Cernik - NK Slavija Pleternica 2:0
15:30 NK Vukovar 91 - NK Podravina 3:2
15:30 NK Nedelišće - NK Karlovac 1:3
15:30 NK Garić Garešnica - NK Graficar Vodovod 1:4
15:30 NK Mladost Molve - NK Konavljanin Cilipi 3:4 aet
15:30 NK Lučko - NK Sračinec 11:1
15:30 NK Vinogradar - NK Oriolik 1:2
03/09/2008 15:30 NK Novalja - Metalac Sisak 0:1
1. Round
23/09/2008 14:30 NK Orijent Rijeka - Hajduk Split 1:4
14:30 NK Karlovac - NK Istra 1961 7:6 pso
14:30 Hrvatski Dragovoljac - NK Međimurje 1:0
24/09/2008 NK Oriolik - Kamen Ingrad dnp
14:30 Metalac Sisak - HNK Rijeka 0:6
14:30 NK Mladost Cernik - NK Varteks 0:1
14:30 NK Zagora Unešić - NK Osijek 2:1
14:30 NK Graficar Vodovod - NK Zagreb 1:3
14:30 HNK Suhopolje - HNK Cibalia 1:2
14:30 NK Lučko - NK Inter Zaprešić 3:5
14:30 NK Moslavina Kutina - HNK Šibenik 2:1
14:30 NK Vukovar 91 - NK Pomorac 0:1
14:30 NK Konavljanin Cilipi - NK Belišce 1:0
14:30 NK Zadar - NK Naftaš HAŠK 3:0
08/10/2008 14:30 NK Gaj Mace - Dinamo Zagreb 1:5
14:30 NK Polet Buševec - Slaven Belupo 0:2
Round of 16
29/10/2008 13:00 Hrvatski Dragovoljac - Dinamo Zagreb 0:6
13:00 NK Konavljanin Cilipi - Hajduk Split 0:2
13:00 NK Pomorac - NK Varteks 2:0
13:00 NK Moslavina Kutina - Slaven Belupo 0:2
13:00 NK Zagora Unešić - NK Karlovac 2:1
13:00 NK Oriolik - HNK Cibalia 0:4
16:00 NK Zadar - HNK Rijeka 4:5 pso
16:00 NK Inter Zaprešić - NK Zagreb 0:2
Quarter-finals
12/11/2008 13:00 NK Pomorac - HNK Cibalia 1:1
13:00 NK Zagora Unešić - Dinamo Zagreb 1:2
16:00 HNK Rijeka - NK Zagreb 2:2
16:00 Hajduk Split - Slaven Belupo 0:0
26/11/2008 16:00 NK Zagreb - HNK Rijeka 4:2 pso
16:00 HNK Cibalia - NK Pomorac 4:2 pso
16:00 Slaven Belupo - Hajduk Split 6:7 pso
10/12/2008 13:00 Dinamo Zagreb - NK Zagora Unešić 5:1
Semi-finals
04/03/2009 14:30 Hajduk Split - HNK Cibalia 4:1
16:00 NK Zagreb - Dinamo Zagreb 0:2
18/03/2009 16:00 Dinamo Zagreb - NK Zagreb 4:1
16:00 HNK Cibalia - Hajduk Split 0:0
Final
13/05/2009 19:15 Dinamo Zagreb - Hajduk Split 3:0
28/05/2009 19:00 Hajduk Split - Dinamo Zagreb 3:4 pso