| Group 2 | 03/03/1999 | Deportivo Cali | - | River Plate | 1:0 | ||||
| Group 2 | 24/03/1999 | River Plate | - | Once Caldas | 3:0 | ||||
| Group 2 | 05/04/1999 | River Plate | - | Deportivo Cali | 2:1 | ||||
| Round of 16 | 13/04/1999 | River Plate | - | LDU Quito | 1:0 |  |
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| Round of 16 | 20/04/1999 | LDU Quito | - | River Plate | 4:5 pso |  |
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| Quarter-finals | 04/05/1999 | River Plate | - | Vélez Sarsfield | 2:0 | ||||
| Quarter-finals | 11/05/1999 | Vélez Sarsfield | - | River Plate | 1:0 | ||||
| Semi-finals | 25/05/1999 | Palmeiras | - | River Plate | 3:0 |
Argentina