| 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 | 2023/10/16 13:00 | NK Krka U19 v Olimpija Ljubljana U19 | D | 0-0 |
| Slovenia U19 League | 2023/10/06 13:30 | Olimpija Ljubljana U19 v NS Mura U19 | W | 2-1 |
| Slovenia U19 League | 2023/09/29 13:30 | NK Bravo U19 v Olimpija Ljubljana U19 | D | 0-0 |
| Slovenia U19 League | 2023/09/24 10:45 | Olimpija Ljubljana U19 v NK Domzale U19 | W | 3-1 |
| Slovenia U19 League | 2023/09/20 14:00 | NK Celje U19 v Olimpija Ljubljana U19 | D | 3-3 |
| Slovenia U19 League | 2023/09/15 14:00 | NK Nafta 1903 U19 v Olimpija Ljubljana U19 | W | 1-2 |
| Slovenia U19 League | 2023/09/01 15:00 | Olimpija Ljubljana U19 v NK Rudar Velenje U19 | L | 0-2 |
| Slovenia U19 League | 2023/08/26 15:00 | ND Ilirija U19 v Olimpija Ljubljana U19 | W | 2-3 |
| Slovenia U19 League | 2023/10/14 13:00 | NK Brinje Grosuplje U19 v NK Aluminij U19 | W | 1-0 |
| Slovenia U19 League | 2023/10/06 13:00 | NK Radomlje U19 v NK Brinje Grosuplje U19 | W | 2-3 |
| Slovenia U19 League | 2023/10/04 14:00 | ND Ilirija U19 v NK Brinje Grosuplje U19 | W | 1-3 |
| Slovenia U19 League | 2023/10/01 13:30 | NK Brinje Grosuplje U19 v ND Gorica U19 | W | 2-0 |
| Slovenia U19 League | 2023/09/25 17:00 | NK Brinje Grosuplje U19 v NK Celje U19 | W | 1-0 |
| Slovenia U19 League | 2023/09/15 14:00 | NK Krka U19 v NK Brinje Grosuplje U19 | L | 3-0 |
| Slovenia U19 League | 2023/08/28 15:00 | NK Bravo U19 v NK Brinje Grosuplje U19 | D | 0-0 |
| Slovenia U19 League | 2023/08/21 15:30 | NK Brinje Grosuplje U19 v NK Domzale U19 | L | 1-2 |