| Wednesday 3rd November 1999 | |||
| English Division OneTable » | |||
| Manchester City | 4-2 | Portsmouth | |
| English Division TwoTable » | |||
| Preston North End | 3-0 | Bournemouth | |
| Stoke City | 0-1 | Notts County | |
| UEFA Champions League First Round Group E | |||
| Molde | 0-1 | Real Madrid | |
| Olympiakos | 1-0 | FC Porto | |
| UEFA Champions League First Round Group F | |||
| Bayern Munich | 1-0 | Rangers | |
| Valencia | 1-0 | PSV Eindhoven | |
| UEFA Champions League First Round Group G | |||
| Sparta Prague | 5-2 | Spartak Moscow | |
| Willem II | 0-0 | Bordeaux | |
| UEFA Champions League First Round Group H | |||
| Chelsea | 2-0 | Hertha BSC Berlin | |
| Galatasaray | 3-2 | AC Milan | |
| Dutch EredivisieTable » | |||
| NEC Nijmegen | 0-4 | Heerenveen | |
» Results : Wednesday 3rd November 1999
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