| 1999-12-19 | CagliarivLecceSerie A · Italy | 0–0 | Serie A · Italy |
| 1999-12-19 | GenclerbirligivBursasporSüper Lig · Turkey | 1–0 | Süper Lig · Turkey |
| 1999-12-19 | Sheffield UnitedvBlackburnChampionship · England | 2–1 | Championship · England |
| 1999-12-19 | ParmavRomaSerie A · Italy | 2–0 | Serie A · Italy |
| 1999-12-19 | CosenzavPistoieseSerie B · Italy | 3–0 | Serie B · Italy |
| 1999-12-19 | ValenciavVallecanoLa Liga · Spain | 3–1 | La Liga · Spain |
| 1999-12-18 | LyonvMetzLigue 1 · France | 2–0 | Ligue 1 · France |
| 1999-12-18 | La CorunavCeltaLa Liga · Spain | 1–0 | La Liga · Spain |
| 1999-12-18 | NancyvSt EtienneLigue 1 · France | 1–0 | Ligue 1 · France |
| 1999-12-18 | MacclesfieldvLeyton OrientLeague Two · England | 1–0 | League Two · England |
| 1999-12-18 | Man CityvSwindonChampionship · England | 3–0 | Championship · England |
| 1999-12-18 | PortsmouthvPort ValeChampionship · England | 0–0 | Championship · England |
| 1999-12-18 | ClydevAlloaLeague One · Scotland | 0–0 | League One · Scotland |
| 1999-12-18 | DenizlisporvGalatasaraySüper Lig · Turkey | 2–4 | Süper Lig · Turkey |
| 1999-12-18 | CelticvDundee UnitedPremiership · Scotland | 4–1 | Premiership · Scotland |
| 1999-12-18 | ExtremaduravAlbaceteLa Liga 2 · Spain | 3–0 | La Liga 2 · Spain |
| 1999-12-18 | Crystal PalacevFulhamChampionship · England | 0–0 | Championship · England |
| 1999-12-18 | ScunthorpevBuryLeague One · England | 0–2 | League One · England |
| 1999-12-18 |  Dominicav Saint LuciaFriendly | 2–1 | Friendly |
| 1999-12-18 | BradfordvNewcastlePremier League · England | 2–0 | Premier League · England |
| 1999-12-18 | LiverpoolvCoventryPremier League · England | 2–0 | Premier League · England |
| 1999-12-18 | ValladolidvAlavesLa Liga · Spain | 1–1 | La Liga · Spain |
| 1999-12-18 | HuddersfieldvGrimsbyChampionship · England | 3–1 | Championship · England |
| 1999-12-18 | MillwallvNotts CountyLeague One · England | 1–0 | League One · England |
| 1999-12-18 | KilmarnockvSt JohnstonePremiership · Scotland | 1–2 | Premiership · Scotland |
| 1999-12-18 | StirlingvStranraerLeague One · Scotland | 2–5 | League One · Scotland |
| 1999-12-18 | FalkirkvMortonChampionship · Scotland | 2–1 | Championship · Scotland |
| 1999-12-18 | ExetervHartlepoolLeague Two · England | 1–2 | League Two · England |
| 1999-12-18 | BoltonvStockportChampionship · England | 0–1 | Championship · England |
| 1999-12-18 | West HamvMan UnitedPremier League · England | 2–4 | Premier League · England |
| 1999-12-18 | MannheimvMainz2. Bundesliga · Germany | 2–1 | 2. Bundesliga · Germany |
| 1999-12-18 | BarivInterSerie A · Italy | 2–1 | Serie A · Italy |
| 1999-12-18 | WatfordvEvertonPremier League · England | 1–3 | Premier League · England |
| 1999-12-18 | PSV EindhovenvHeerenveenEredivisie · Netherlands | 0–1 | Eredivisie · Netherlands |
| 1999-12-18 | RotherhamvDarlingtonLeague Two · England | 2–1 | League Two · England |
| 1999-12-18 | Albion RvsvDumbartonLeague Two · Scotland | 3–0 | League Two · Scotland |
| 1999-12-18 | Real MadridvEspanolLa Liga · Spain | 2–1 | La Liga · Spain |
| 1999-12-18 | StokevBristol RvsLeague One · England | 1–2 | League One · England |
| 1999-12-18 | ChestervHalifaxLeague Two · England | 2–1 | League Two · England |
| 1999-12-18 | LincolnvShrewsburyLeague Two · England | 1–2 | League Two · England |
| 1999-12-18 | WiganvBrentfordLeague One · England | 1–0 | League One · England |
| 1999-12-18 | LeicestervDerbyPremier League · England | 0–1 | Premier League · England |
| 1999-12-18 | BadajozvSalamancaLa Liga 2 · Spain | 2–2 | La Liga 2 · Spain |
| 1999-12-18 | ReadingvWrexhamLeague One · England | 2–2 | League One · England |
| 1999-12-18 | Munich 1860vKaiserslauternBundesliga · Germany | 2–1 | Bundesliga · Germany |
| 1999-12-18 | UlmvEin FrankfurtBundesliga · Germany | 3–0 | Bundesliga · Germany |
| 1999-12-18 | NantesvBastiaLigue 1 · France | 1–1 | Ligue 1 · France |
| 1999-12-18 | MarseillevLensLigue 1 · France | 1–2 | Ligue 1 · France |
| 1999-12-18 |  MonacovMontpellierLigue 1 · France | 1–0 | Ligue 1 · France |
| 1999-12-18 | AnkaragucuvKocaelisporSüper Lig · Turkey | 3–2 | Süper Lig · Turkey |