| 1er tour | 16.09.1999 | AS Roma | - | Vitória Setúbal | 7:0 |  |
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| 1er tour | 30.09.1999 | Vitória Setúbal | - | AS Roma | 1:0 | ||||
| 3e tour | 25.11.1999 | AS Roma | - | Newcastle United | 1:0 | ||||
| 3e tour | 09.12.1999 | Newcastle United | - | AS Roma | 0:0 | ||||
| tour des 16 | 02.03.2000 | AS Roma | - | Leeds United | 0:0 | ||||
| tour des 16 | 09.03.2000 | Leeds United | - | AS Roma | 1:0 |
Italie