| 1. Round | 15/09/1999 | AS Roma | - | Vitória Setúbal | 7:0 |  |
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| 1. Round | 29/09/1999 | Vitória Setúbal | - | AS Roma | 1:0 | ||||
| 3. Round | 24/11/1999 | AS Roma | - | Newcastle United | 1:0 | ||||
| 3. Round | 08/12/1999 | Newcastle United | - | AS Roma | 0:0 | ||||
| Round of 16 | 01/03/2000 | AS Roma | - | Leeds United | 0:0 | ||||
| Round of 16 | 08/03/2000 | Leeds United | - | AS Roma | 1:0 |
Italy