[5] Tabor Sezana 1-2 Olimpija Ljubljana [2] 2019-08-31 15:00
Stadium: Rajko Stolfa Stadium Round: 8
Referee: Nejc Kajtazovic Home Manager: Andrej Razdrh Away Manager: Safet Hadzic
Home History
| Slovenia Prva Liga | 2019/08/25 16:00 | NK Rudar Velenje v Tabor Sezana | D | 2-2 |
| Slovenia Prva Liga | 2019/08/17 15:00 | Tabor Sezana v NK Triglav Kranj | W | 2-0 |
| Slovenia Cup | 2019/08/14 14:00 | SD Videm v Tabor Sezana | W | 1-4 |
| Slovenia Prva Liga | 2019/08/10 18:15 | NK Maribor v Tabor Sezana | L | 4-2 |
| Slovenia Prva Liga | 2019/08/04 15:30 | Tabor Sezana v NK Domzale | W | 2-1 |
| Slovenia Prva Liga | 2019/07/28 15:30 | NK Bravo v Tabor Sezana | L | 1-0 |
| Slovenia Prva Liga | 2019/07/20 16:00 | Tabor Sezana v NK Celje | W | 1-0 |
| Slovenia Prva Liga | 2019/07/13 16:00 | Tabor Sezana v NK Aluminij | L | 0-2 |
Away History
| World Club Friendlies | 2019/08/28 15:36 | Olimpija Ljubljana v El Gounah | L | 1-4 |
| Slovenia Prva Liga | 2019/08/24 18:15 | Olimpija Ljubljana v NS Mura | D | 1-1 |
| Slovenia Prva Liga | 2019/08/18 18:15 | NK Aluminij v Olimpija Ljubljana | L | 1-0 |
| Slovenia Prva Liga | 2019/08/11 18:10 | NK Rudar Velenje v Olimpija Ljubljana | W | 0-3 |
| Slovenia Prva Liga | 2019/08/04 18:15 | Olimpija Ljubljana v NK Triglav Kranj | W | 4-2 |
| UEFA Europa League Qualifying | 2019/08/01 18:00 | Olimpija Ljubljana v Yeni Malatyaspor | L | 0-1 |
| Slovenia Prva Liga | 2019/07/28 18:30 | NK Maribor v Olimpija Ljubljana | D | 0-0 |
| UEFA Europa League Qualifying | 2019/07/25 17:00 | Yeni Malatyaspor v Olimpija Ljubljana | D | 2-2 |