Head to Head
| Croatia U19 League | 2019/11/24 12:00 | NK Osijek U19 v Hrvatski Dragovoljac U19 | L | 3-1 |
| Croatia U19 League | 2019/05/27 13:00 | NK Osijek U19 v Hrvatski Dragovoljac U19 | L | 4-1 |
| Croatia U19 League | 2018/12/02 12:00 | Hrvatski Dragovoljac U19 v NK Osijek U19 | L | 1-5 |
| Croatia U19 League | 2018/05/16 14:00 | Hrvatski Dragovoljac U19 v NK Osijek U19 | L | 0-3 |
| Croatia U19 League | 2017/09/09 13:50 | NK Osijek U19 v Hrvatski Dragovoljac U19 | L | 4-1 |
| Croatia U19 League | 2016/10/01 10:48 | NK Osijek U19 v Hrvatski Dragovoljac U19 | D | 0-0 |
Home History
| Croatia U19 League | 2021/04/24 08:00 | NK Inter-Zapresic U19 v Hrvatski Dragovoljac U19 | L | 1-0 |
| Croatia U19 League | 2021/04/17 12:00 | Hrvatski Dragovoljac U19 v Istra 1961 U19 | W | 3-1 |
| Croatia U19 League | 2021/04/10 12:00 | NK Rudes U19 v Hrvatski Dragovoljac U19 | L | 1-0 |
| Croatia U19 League | 2021/03/13 14:00 | NK Varazdin U19 v Hrvatski Dragovoljac U19 | D | 2-2 |
| Croatia U19 League | 2021/03/06 09:00 | Hrvatski Dragovoljac U19 v NK Lokomotiva Zagreb U19 | L | 0-2 |
| Croatia U19 League | 2021/02/27 11:00 | Hrvatski Dragovoljac U19 v Hajduk Split U19 | L | 0-1 |
| Croatia U19 League | 2020/12/13 12:30 | Hrvatski Dragovoljac U19 v NK Dugopolje U19 | D | 1-1 |
| Croatia U19 League | 2020/12/08 11:00 | Slaven Koprivnica U19 v Hrvatski Dragovoljac U19 | L | 5-1 |
Away History
| Croatia U19 League | 2021/04/24 11:00 | NK Osijek U19 v Hajduk Split U19 | L | 0-2 |
| Croatia U19 League | 2021/04/17 11:30 | Slaven Koprivnica U19 v NK Osijek U19 | L | 2-1 |
| Croatia U19 League | 2021/04/10 09:00 | NK Osijek U19 v HNK Rijeka U19 | W | 1-0 |
| Croatia U19 League | 2021/03/21 10:00 | NK Dugopolje U19 v NK Osijek U19 | L | 3-1 |
| Croatia U19 League | 2021/03/20 09:00 | NK Dugopolje U19 v NK Osijek U19 | L | 3-1 |
| Croatia U19 League | 2021/03/14 13:30 | NK Osijek U19 v Dinamo Zagreb U19 | D | 1-1 |
| Croatia U19 League | 2021/03/13 09:00 | NK Osijek U19 v Dinamo Zagreb U19 | D | 1-1 |
| Croatia U19 League | 2021/03/06 12:00 | NK Sesvete U19 v NK Osijek U19 | L | 2-1 |