| Friday 5th November 1999 | |||
| English Division OneTable » | |||
| Port Vale | 1-0 | Crewe Alexandra | |
| English Division ThreeTable » | |||
| Swansea City | 3-1 | Halifax Town | |
| German BundesligaTable » | |||
| Hansa Rostock | 3-3 | SV Hamburg | |
| SC Freiburg | 3-0 | MSV Duisburg | |
| Dutch EredivisieTable » | |||
| FC Utrecht | 2-1 | Fortuna Sittard | |
| Belgian Jupiler LeagueTable » | |||
| Charleroi | 0-2 | Club Brugge | |
| Portuguese LigaTable » | |||
| Vitoria Guimaraes | 4-2 | Belenenses | |
| Austrian BundesligaTable » | |||
| LASK Linz | 1-1 | Ried | |
| Republic of Ireland Premier DivisionTable » | |||
| Bohemians | 0-2 | Waterford United | |
| Galway United | 0-0 | Shelbourne | |
| UCD | 1-1 | Sligo Rovers | |
» Results : Friday 5th November 1999
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