| Slovenia U19 League | 2021/03/31 14:00 | ND Ilirija U19 v NK Brinje Grosuplje U19 | W | 1-2 |
| Slovenia U19 League | 2021/03/24 14:00 | NK Brinje Grosuplje U19 v NK Drava Ptuj U19 | D | 1-1 |
| Slovenia U19 League | 2020/10/10 11:00 | NK Brinje Grosuplje U19 v NK Radomlje U19 | L | 0-1 |
| Slovenia U19 League | 2020/09/20 14:00 | NK Noga Triglav U19 v NK Brinje Grosuplje U19 | W | 1-2 |
| Slovenia U19 League | 2020/09/09 14:30 | NK Brinje Grosuplje U19 v NK Domzale U19 | L | 0-3 |
| Slovenia U19 League | 2020/08/19 15:00 | NK Brinje Grosuplje U19 v FC Koper U19 | L | 1-4 |
| Slovenia U19 League | 2020/08/15 11:00 | NS Mura U19 v NK Brinje Grosuplje U19 | W | 2-3 |
| Slovenia U19 League | 2021/03/24 13:00 | Olimpija Ljubljana U19 v NK Bravo U19 | D | 1-1 |
| Slovenia U19 League | 2020/10/11 11:00 | NK Domzale U19 v Olimpija Ljubljana U19 | D | 1-1 |
| Slovenia U19 League | 2020/09/13 15:30 | NK Celje U19 v Olimpija Ljubljana U19 | W | 1-2 |
| Slovenia U19 League | 2020/09/09 14:30 | Olimpija Ljubljana U19 v NK Maribor U19 | W | 5-1 |
| Slovenia U19 League | 2020/03/01 12:00 | NK Aluminij U19 v Olimpija Ljubljana U19 | D | 1-1 |
| Slovenia U19 League | 2019/12/01 12:00 | NK Celje U19 v Olimpija Ljubljana U19 | W | 0-1 |
| Slovenia U19 League | 2019/11/28 13:00 | NS Mura U19 v Olimpija Ljubljana U19 | W | 2-3 |
| Slovenia U19 League | 2019/10/02 14:00 | Olimpija Ljubljana U19 v NK Aluminij U19 | W | 2-1 |