Gameplan
| Date | Round | Match | Match | Res. | Attendance | |
|---|---|---|---|---|---|---|
| 21.01.1999 |  | Round of 16 First leg | Real Madrid - Villarreal | RMA - VIL | 2:0 | |
| 23.02.1999 | | Quarter-finals 2nd leg | Real Madrid - Racing | RMA - RAC | 1:0 | |
| 03.03.1999 |  | Quarter-finals First leg | Real Madrid - Dynamo Kyiv | RMA - KYI | 1:1 | 35.183 |
| 16.06.1999 | | Semi-finals 2nd leg | Real Madrid - Valencia | RMA - VCF | 2:1 | |
| 21.09.1999 | | Preliminary Gr. E | Real Madrid - Molde FK | RMA - MOL | 4:1 | 15.000 |
| 28.09.1999 | | Preliminary Gr. E | Real Madrid - FC Porto | RMA - POR | 3:1 | 41.000 |
| 26.10.1999 | | Preliminary Gr. E | Real Madrid - Olympiacos FC | RMA - OLY | 3:0 | 23.000 |
| 07.12.1999 | | Intermediate Gr. C | Real Madrid - Rosenborg | RMA - RBK | 3:1 | 35.000 |