Stadium: Theodoros Kolokotronis Stadium Round: 4
Referee: Dimitris Karantonis Home Manager: Milan Rastavac Away Manager: Pedro Martins
| Greece Super League 1 | 2021/05/09 14:15 | Asteras Tripolis v Olympiacos | D | 0-0 |
| Greece Super League 1 | 2021/04/21 14:15 | Olympiacos v Asteras Tripolis | L | 1-0 |
| Greece Super League 1 | 2021/01/06 17:30 | Asteras Tripolis v Olympiacos | L | 0-4 |
| Greece Super League 1 | 2020/09/18 17:30 | Olympiacos v Asteras Tripolis | L | 3-0 |
| Greece Super League 1 | 2019/12/15 17:30 | Asteras Tripolis v Olympiacos | L | 0-5 |
| Greece Super League 1 | 2019/08/24 18:30 | Olympiacos v Asteras Tripolis | L | 1-0 |
| Greece Super League 1 | 2019/01/27 17:30 | Asteras Tripolis v Olympiacos | L | 0-2 |
| Greece Super League 1 | 2018/09/16 17:30 | Olympiacos v Asteras Tripolis | L | 2-1 |
| Europe Friendlies | 2021/08/28 17:00 | Panathinaikos v Asteras Tripolis | D | 1-1 |
| Europe Friendlies | 2021/08/21 17:00 | AEK Athens v Asteras Tripolis | W | 0-1 |
| Europe Friendlies | 2021/08/14 16:00 | Asteras Tripolis v Giannina | W | 1-0 |
| Europe Friendlies | 2021/08/08 16:00 | Asteras Tripolis v Atromitos Athinon | W | 4-1 |
| Europe Friendlies | 2021/08/04 16:00 | Asteras Tripolis v Apollon Smyrnis | W | 4-0 |
| Europe Friendlies | 2021/08/01 16:30 | Asteras Tripolis v Ionikos Nikea | W | 4-0 |
| Greece Super League 1 | 2021/05/16 16:30 | PAOK Salonika v Asteras Tripolis | W | 0-1 |
| Greece Super League 1 | 2021/05/12 16:30 | Asteras Tripolis v AEK Athens | D | 1-1 |
| UEFA Europa League Qualifying | 2021/08/26 18:45 | Slovan Bratislava v Olympiacos | D | 2-2 |
| UEFA Europa League Qualifying | 2021/08/19 19:00 | Olympiacos v Slovan Bratislava | W | 3-0 |
| UEFA Champions League Qualifying | 2021/08/10 18:00 | Ludogorets Razgrad v Olympiacos | L | 6-3 |
| UEFA Champions League Qualifying | 2021/08/03 19:00 | Olympiacos v Ludogorets Razgrad | D | 1-1 |
| UEFA Champions League Qualifying | 2021/07/28 17:00 | Neftchi Baku v Olympiacos | W | 0-1 |
| UEFA Champions League Qualifying | 2021/07/21 19:00 | Olympiacos v Neftchi Baku | W | 1-0 |
| Europe Friendlies | 2021/07/14 18:00 | Olympiacos v Aris Salonika | W | 3-0 |
| Europe Friendlies | 2021/07/03 14:00 | Olympiacos v CS U Craiova | W | 2-0 |