Head to Head
| Croatia U19 League | 2022/12/10 09:00 | NK Dugopolje U19 v NK Osijek U19 | L | 2-4 |
| Croatia U19 League | 2022/08/14 08:13 | NK Osijek U19 v NK Dugopolje U19 | L | 3-2 |
| Croatia U19 League | 2022/05/28 08:00 | NK Osijek U19 v NK Dugopolje U19 | D | 3-3 |
| Croatia U19 League | 2021/11/28 09:00 | NK Dugopolje U19 v NK Osijek U19 | W | 2-1 |
| Croatia U19 League | 2021/03/21 10:00 | NK Dugopolje U19 v NK Osijek U19 | W | 3-1 |
| Croatia U19 League | 2021/03/20 09:00 | NK Dugopolje U19 v NK Osijek U19 | W | 3-1 |
| Croatia U19 League | 2020/09/19 09:00 | NK Osijek U19 v NK Dugopolje U19 | L | 2-1 |
| Croatia U19 League | 2020/02/22 09:00 | NK Osijek U19 v NK Dugopolje U19 | L | 3-0 |
Home History
| Croatia U19 League | 2023/09/29 09:00 | NK Varazdin U19 v NK Dugopolje U19 | W | 0-1 |
| Croatia U19 League | 2023/09/23 08:00 | NK Dugopolje U19 v HNK Cibalia U19 | L | 1-3 |
| Croatia U19 League | 2023/09/16 15:00 | NK Lokomotiva Zagreb U19 v NK Dugopolje U19 | L | 3-1 |
| Croatia U19 League | 2023/09/02 08:00 | NK Dugopolje U19 v Dinamo Zagreb U19 | W | 2-1 |
| Croatia U19 League | 2023/08/26 15:00 | HNK Gorica U19 v NK Dugopolje U19 | D | 1-1 |
| Croatia U19 League | 2023/08/19 08:00 | NK Dugopolje U19 v Istra 1961 U19 | L | 1-5 |
| Croatia U19 League | 2023/08/16 15:00 | NK Rudes U19 v NK Dugopolje U19 | L | 1-0 |
| Croatia U19 League | 2023/08/12 07:00 | NK Dugopolje U19 v Hajduk Split U19 | L | 1-2 |
Away History
| Croatia U19 League | 2023/09/23 09:00 | HNK Rijeka U19 v NK Osijek U19 | D | 1-1 |
| Croatia U19 League | 2023/09/02 14:00 | NK Sesvete U19 v NK Osijek U19 | W | 0-1 |
| Croatia U19 League | 2023/08/19 14:00 | NK Osijek U19 v Slaven Koprivnica U19 | W | 7-1 |
| Croatia U19 League | 2023/08/16 15:00 | NK Varazdin U19 v NK Osijek U19 | W | 1-2 |
| Croatia U19 League | 2023/08/12 08:00 | NK Osijek U19 v HNK Cibalia U19 | W | 5-0 |
| Europe Friendlies | 2023/06/11 10:00 | NK Osijek U19 v Partizan Belgrade U19 | L | 2-3 |
| Europe Friendlies | 2023/06/10 09:00 | Crvena Zvezda U19 v NK Osijek U19 | W | 0-1 |
| Europe Friendlies | 2023/06/09 09:00 | HNK Sibenik U19 v NK Osijek U19 | W | 0-2 |