| Dates |
Season |
Cup |
Round |
Match |
Result |
| 22.10.1997 |
1997/98 |
CL |
Group stage |
Real Madrid - Olympiacos Pireaus |
5:1 (2:1) |
| 05.11.1997 |
1997/98 |
CL |
Group stage |
Olympiacos Pireaus - Real Madrid |
0:0 (0:0) |
| 15.09.1999 |
1999/00 |
CL |
Group stage 1 |
Olympiacos Pireaus - Real Madrid |
3:3 (1:2) |
| 26.10.1999 |
1999/00 |
CL |
Group stage 1 |
Real Madrid - Olympiacos Pireaus |
3:0 (1:0) |
| 28.09.2005 |
2005/06 |
CL |
Group stage |
Real Madrid - Olympiacos Pireaus |
2:1 (1:0) |
| 06.12.2005 |
2005/06 |
CL |
Group stage |
Olympiacos Pireaus - Real Madrid |
2:1 (0:1) |
| 24.10.2007 |
2007/08 |
CL |
Group stage |
Real Madrid - Olympiacos Pireaus |
4:2 (1:1) |
| 06.11.2007 |
2007/08 |
CL |
Group stage |
Olympiacos Pireaus - Real Madrid |
0:0 (0:0) |
| 26.11.2025 |
2025/26 |
CL |
Group stage |
Olympiacos Pireaus - Real Madrid |
3:4 (1:3) |
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