| Preliminary Gr. H | 14/09/1999 | Chelsea FC | - | AC Milan | 0:0 | ||||
| Preliminary Gr. H | 20/09/1999 | Hertha BSC | - | Chelsea FC | 2:1 |  |
|||
| Preliminary Gr. H | 27/09/1999 | Chelsea FC | - | Galatasaray | 1:0 | ||||
| Preliminary Gr. H | 19/10/1999 | Galatasaray | - | Chelsea FC | 0:5 | ||||
| Preliminary Gr. H | 25/10/1999 | AC Milan | - | Chelsea FC | 1:1 | ||||
| Preliminary Gr. H | 02/11/1999 | Chelsea FC | - | Hertha BSC | 2:0 | ||||
| Intermediate Gr. D | 23/11/1999 | Chelsea FC | - | Feyenoord | 3:1 |  |
|||
| Intermediate Gr. D | 06/12/1999 | Lazio Roma | - | Chelsea FC | 0:0 | ||||
| Intermediate Gr. D | 07/03/2000 | Chelsea FC | - | Olympique Marseille | 1:0 | ||||
| Intermediate Gr. D | 13/03/2000 | Feyenoord | - | Chelsea FC | 1:3 | ||||
| Intermediate Gr. D | 21/03/2000 | Chelsea FC | - | Lazio Roma | 1:2 | ||||
| Quarter-finals | 04/04/2000 | Chelsea FC | - | FC Barcelona | 3:1 | ||||
| Quarter-finals | 17/04/2000 | FC Barcelona | - | Chelsea FC | 5:1 aet |  |
Nigeria