1. Round | 19/07/2019 | NK Osijek | - | Slaven Belupo | 2:0 | ||||
3. Round | 04/08/2019 | NK Osijek | - | NK Inter Zaprešić | 3:1 | ||||
4. Round | 09/08/2019 | NK Osijek | - | Dinamo Zagreb | 0:0 | ||||
5. Round | 18/08/2019 | HNK Rijeka | - | NK Osijek | 1:1 | ||||
6. Round | 25/08/2019 | NK Osijek | - | Hajduk Split | 1:0 | ||||
7. Round | 31/08/2019 | NK Istra 1961 | - | NK Osijek | 0:0 | ||||
8. Round | 15/09/2019 | NK Osijek | - | NK Varaždin | 2:2 | ||||
17. Round | 30/11/2019 | NK Varaždin | - | NK Osijek | 1:1 |