| Wednesday 20th October 1999 | |||
| English Division OneTable » | |||
| Blackburn Rovers | 1-1 | Crystal Palace | |
| English Division TwoTable » | |||
| Reading | 2-0 | Bury | |
| Scottish Premier LeagueTable » | |||
| Motherwell | 5-6 | Aberdeen | |
| UEFA Champions League First Round Group E | |||
| FC Porto | 2-1 | Real Madrid | |
| Molde | 3-2 | Olympiakos | |
| UEFA Champions League First Round Group F | |||
| Rangers | 4-1 | PSV Eindhoven | |
| Valencia | 1-1 | Bayern Munich | |
| UEFA Champions League First Round Group G | |||
| Spartak Moscow | 1-2 | Bordeaux | |
| Willem II | 3-4 | Sparta Prague | |
| UEFA Champions League First Round Group H | |||
| Galatasaray | 0-5 | Chelsea | |
| Hertha BSC Berlin | 1-0 | AC Milan | |
| Danish SuperligaenTable » | |||
| Esbjerg | 0-0 | AaB Aalborg | |
» Results : Wednesday 20th October 1999
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