| Slovenia U19 League | 2024/05/06 15:30 | NK Brinje Grosuplje U19 v Olimpija Ljubljana U19 | L | 2-0 |
| Slovenia U19 League | 2023/10/22 13:00 | Olimpija Ljubljana U19 v NK Brinje Grosuplje U19 | W | 1-0 |
| Slovenia U19 League | 2023/03/04 14:00 | Olimpija Ljubljana U19 v NK Brinje Grosuplje U19 | W | 2-0 |
| Slovenia U19 League | 2022/08/20 17:00 | NK Brinje Grosuplje U19 v Olimpija Ljubljana U19 | W | 1-3 |
| Slovenia U19 League | 2022/03/06 14:00 | NK Brinje Grosuplje U19 v Olimpija Ljubljana U19 | L | 3-2 |
| Slovenia U19 League | 2021/05/01 10:00 | NK Brinje Grosuplje U19 v Olimpija Ljubljana U19 | W | 0-2 |
| Slovenia U19 League | 2025/04/07 13:30 | NS Mura U19 v Olimpija Ljubljana U19 | W | 1-2 |
| Slovenia U19 League | 2025/03/28 14:00 | Olimpija Ljubljana U19 v NK Celje U19 | D | 1-1 |
| Slovenia U19 League | 2025/03/14 14:00 | NK Domzale U19 v Olimpija Ljubljana U19 | L | 2-0 |
| Slovenia U19 League | 2025/03/10 14:30 | Olimpija Ljubljana U19 v NK Maribor U19 | W | 2-1 |
| Slovenia U19 League | 2025/02/28 14:00 | NK Rudar Velenje U19 v Olimpija Ljubljana U19 | L | 2-1 |
| Slovenia U19 League | 2025/02/24 14:00 | ND Gorica U19 v Olimpija Ljubljana U19 | W | 0-1 |
| Slovenia U19 League | 2024/11/30 13:00 | ND Ilirija U19 v Olimpija Ljubljana U19 | L | 3-1 |
| Slovenia U19 League | 2024/11/25 13:00 | NK Radomlje U19 v Olimpija Ljubljana U19 | L | 3-2 |
| Slovenia U19 League | 2025/04/07 16:00 | NK Brinje Grosuplje U19 v NK Aluminij U19 | W | 5-2 |
| Slovenia U19 League | 2025/03/30 15:00 | NK Brinje Grosuplje U19 v FC Koper U19 | D | 0-0 |
| Slovenia U19 League | 2025/03/15 12:00 | NK Brinje Grosuplje U19 v ND Gorica U19 | D | 1-1 |
| Slovenia U19 League | 2025/03/02 14:00 | NK Krka U19 v NK Brinje Grosuplje U19 | W | 0-4 |
| Slovenia U19 League | 2025/02/23 13:00 | NK Brinje Grosuplje U19 v NK IB 1975 Ljubljana U19 | W | 2-1 |
| Slovenia U19 League | 2024/12/06 13:00 | NS Mura U19 v NK Brinje Grosuplje U19 | L | 1-0 |
| Slovenia U19 League | 2024/11/30 13:00 | NK Brinje Grosuplje U19 v NK Celje U19 | D | 1-1 |
| Slovenia U19 League | 2024/11/24 13:00 | NK Brinje Grosuplje U19 v NK Domzale U19 | D | 2-2 |