| Friday 15th October 1999 | |||
| English Division TwoTable » | |||
| Cambridge United | 5-2 | Colchester United | |
| German BundesligaTable » | |||
| Arminia Bielefeld | 0-2 | Borussia Dortmund | |
| Bayer Leverkusen | 4-1 | Ulm | |
| French Ligue 1Table » | |||
| Marseille | 0-1 | Lyon | |
| Dutch EredivisieTable » | |||
| Roda JC | 2-1 | Feyenoord | |
| Portuguese LigaTable » | |||
| FC Porto | 4-2 | Uniao Leiria | |
| Turkish Super LigTable » | |||
| Galatasaray | 2-0 | Antalyaspor | |
| Austrian BundesligaTable » | |||
| Wacker Innsbruck | 3-0 | Austria Lustenau | |
| Republic of Ireland Premier DivisionTable » | |||
| Drogheda United | 1-2 | St Patrick's Ath | |
| Galway United | 1-3 | Finn Harps | |
| Waterford United | 0-0 | Shelbourne | |
» Results : Friday 15th October 1999
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