| Preliminary Gr. D | 13/09/1999 | Manchester United | - | Croatia Zagreb | 0:0 | ||||
| Preliminary Gr. D | 21/09/1999 | Sturm Graz | - | Manchester United | 0:3 |  |
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| Preliminary Gr. D | 28/09/1999 | Manchester United | - | Olympique Marseille | 2:1 | ||||
| Preliminary Gr. D | 18/10/1999 | Olympique Marseille | - | Manchester United | 1:0 |  |
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| Preliminary Gr. D | 26/10/1999 | Croatia Zagreb | - | Manchester United | 1:2 | ||||
| Intermediate Gr. B | 22/11/1999 | ACF Fiorentina | - | Manchester United | 2:0 | ||||
| Intermediate Gr. B | 07/12/1999 | Manchester United | - | Valencia CF | 3:0 | ||||
| Intermediate Gr. B | 06/03/2000 | Girondins Bordeaux | - | Manchester United | 1:2 | ||||
| Intermediate Gr. B | 14/03/2000 | Manchester United | - | ACF Fiorentina | 3:1 | |
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| Quarter-finals | 03/04/2000 | Real Madrid | - | Manchester United | 0:0 | ||||
| Quarter-finals | 18/04/2000 | Manchester United | - | Real Madrid | 2:3 |
Trinidad & Tobago
