| Slovenia U19 League | 2023/10/22 13:00 | Olimpija Ljubljana U19 v NK Brinje Grosuplje U19 | L | 1-0 |
| Slovenia U19 League | 2023/03/04 14:00 | Olimpija Ljubljana U19 v NK Brinje Grosuplje U19 | L | 2-0 |
| Slovenia U19 League | 2022/08/20 17:00 | NK Brinje Grosuplje U19 v Olimpija Ljubljana U19 | L | 1-3 |
| Slovenia U19 League | 2022/03/06 14:00 | NK Brinje Grosuplje U19 v Olimpija Ljubljana U19 | W | 3-2 |
| Slovenia U19 League | 2021/05/01 10:00 | NK Brinje Grosuplje U19 v Olimpija Ljubljana U19 | L | 0-2 |
| Slovenia U19 League | 2024/04/28 15:00 | NK Aluminij U19 v NK Brinje Grosuplje U19 | L | 3-1 |
| Slovenia U19 League | 2024/04/19 12:00 | NK Brinje Grosuplje U19 v NK Radomlje U19 | W | 4-0 |
| Slovenia U19 League | 2024/04/15 15:00 | ND Gorica U19 v NK Brinje Grosuplje U19 | D | 0-0 |
| Slovenia U19 League | 2024/04/07 15:30 | NK Celje U19 v NK Brinje Grosuplje U19 | L | 4-0 |
| Slovenia U19 League | 2024/04/01 12:00 | NK Brinje Grosuplje U19 v NK Krka U19 | L | 1-2 |
| Slovenia U19 League | 2024/03/16 12:30 | NS Mura U19 v NK Brinje Grosuplje U19 | W | 1-2 |
| Slovenia U19 League | 2024/03/11 14:00 | NK Brinje Grosuplje U19 v NK Bravo U19 | L | 1-2 |
| Slovenia U19 League | 2024/02/28 12:00 | NK Domzale U19 v NK Brinje Grosuplje U19 | L | 2-1 |
| Slovenia U19 League | 2024/04/26 15:00 | Olimpija Ljubljana U19 v NK Krka U19 | W | 1-0 |
| Slovenia U19 League | 2024/04/22 14:00 | NS Mura U19 v Olimpija Ljubljana U19 | L | 3-1 |
| Slovenia U19 League | 2024/04/13 15:00 | Olimpija Ljubljana U19 v NK Bravo U19 | W | 1-0 |
| Slovenia U19 League | 2024/04/05 14:00 | NK Domzale U19 v Olimpija Ljubljana U19 | L | 4-0 |
| Slovenia U19 League | 2024/04/01 14:00 | Olimpija Ljubljana U19 v NK Nafta 1903 U19 | W | 8-2 |
| Slovenia U19 League | 2024/03/15 16:00 | NK Rudar Velenje U19 v Olimpija Ljubljana U19 | W | 0-4 |
| Slovenia U19 League | 2024/02/25 13:00 | Olimpija Ljubljana U19 v FC Koper U19 | D | 2-2 |
| Slovenia U19 League | 2023/12/08 15:00 | NK Maribor U19 v Olimpija Ljubljana U19 | D | 1-1 |