| 1999-12-04 | Ross CountyvPartickLeague One · Scotland | 2–1 | League One · Scotland |
| 1999-12-04 | BrentfordvBristol RvsLeague One · England | 0–3 | League One · England |
| 1999-12-04 | BoltonvTranmereChampionship · England | 2–3 | Championship · England |
| 1999-12-04 | SwanseavYorkLeague Two · England | 1–0 | League Two · England |
| 1999-12-04 | Port ValevBlackburnChampionship · England | 0–0 | Championship · England |
| 1999-12-04 | LiersevSt TruidenPro League · Belgium | 0–0 | Pro League · Belgium |
| 1999-12-04 | StenhousemuirvAlloaLeague One · Scotland | 1–3 | League One · Scotland |
| 1999-12-04 | BesiktasvAdanasporSüper Lig · Turkey | 0–1 | Süper Lig · Turkey |
| 1999-12-04 | AyrvDunfermlineChampionship · Scotland | 2–3 | Championship · Scotland |
| 1999-12-04 | PlymouthvSouthendLeague Two · England | 3–1 | League Two · England |
| 1999-12-04 | FulhamvBirminghamChampionship · England | 0–0 | Championship · England |
| 1999-12-04 | GueugnonvChateaurouxLigue 2 · France | 1–1 | Ligue 2 · France |
| 1999-12-04 | MVV MaastrichtvTwenteEredivisie · Netherlands | 0–2 | Eredivisie · Netherlands |
| 1999-12-04 | CambridgevBournemouthLeague One · England | 0–2 | League One · England |
| 1999-12-04 | TorquayvShrewsburyLeague Two · England | 3–1 | League Two · England |
| 1999-12-04 | GuingampvLavalLigue 2 · France | 2–2 | Ligue 2 · France |
| 1999-12-04 | CharleroivAalstPro League · Belgium | 0–1 | Pro League · Belgium |
| 1999-12-04 | Ath BilbaovSociedadLa Liga · Spain | 1–1 | La Liga · Spain |
| 1999-12-04 | HullvExeterLeague Two · England | 4–0 | League Two · England |
| 1999-12-04 | LutonvNotts CountyLeague One · England | 2–2 | League One · England |
| 1999-12-04 | AlvercavFarensePrimeira Liga · Portugal | 0–1 | Primeira Liga · Portugal |
| 1999-12-04 | LeicestervArsenalPremier League · England | 0–3 | Premier League · England |
| 1999-12-04 | Paris SGvRennesLigue 1 · France | 1–0 | Ligue 1 · France |
| 1999-12-04 | LommelvClub BruggePro League · Belgium | 0–0 | Pro League · Belgium |
| 1999-12-04 | TenerifevAth Madrid BLa Liga 2 · Spain | 2–1 | La Liga 2 · Spain |
| 1999-12-04 | NorthamptonvMacclesfieldLeague Two · England | 2–0 | League Two · England |
| 1999-12-04 | AmiensvNimesLigue 2 · France | 0–0 | Ligue 2 · France |
| 1999-12-04 | LillevNiceLigue 2 · France | 1–0 | Ligue 2 · France |
| 1999-12-04 | CrewevCrystal PalaceChampionship · England | 2–0 | Championship · England |
| 1999-12-04 | ScunthorpevWiganLeague One · England | 1–2 | League One · England |
| 1999-12-04 | StranraervArbroathLeague One · Scotland | 2–2 | League One · Scotland |
| 1999-12-04 | ClydebankvLivingstonChampionship · Scotland | 1–5 | Championship · Scotland |
| 1999-12-04 | LorientvLouhans-Cuis.Ligue 2 · France | 5–1 | Ligue 2 · France |
| 1999-12-04 | SunderlandvChelseaPremier League · England | 4–1 | Premier League · England |
| 1999-12-04 | St MirrenvFalkirkChampionship · Scotland | 2–1 | Championship · Scotland |
| 1999-12-04 | CannesvWasquehalLigue 2 · France | 0–0 | Ligue 2 · France |
| 1999-12-04 | HerthavUlmBundesliga · Germany | 3–0 | Bundesliga · Germany |
| 1999-12-04 | BelenensesvBenficaPrimeira Liga · Portugal | 0–0 | Primeira Liga · Portugal |
| 1999-12-04 | PerugiavLazioSerie A · Italy | 0–2 | Serie A · Italy |
| 1999-12-04 | Queens ParkvEast FifeLeague Two · Scotland | 0–1 | League Two · Scotland |
| 1999-12-04 | RotherhamvLincolnLeague Two · England | 1–1 | League Two · England |
| 1999-12-04 | AlbacetevLleidaLa Liga 2 · Spain | 2–2 | La Liga 2 · Spain |
| 1999-12-04 |  MonacovLensLigue 1 · France | 2–0 | Ligue 1 · France |
| 1999-12-04 | NorwichvWest BromChampionship · England | 2–1 | Championship · England |
| 1999-12-04 | ValencevToulouseLigue 2 · France | 0–2 | Ligue 2 · France |
| 1999-12-04 | CelticvHibernianPremiership · Scotland | 4–0 | Premiership · Scotland |
| 1999-12-04 | AuxerrevMetzLigue 1 · France | 1–1 | Ligue 1 · France |
| 1999-12-04 | Bristol CityvReadingLeague One · England | 3–1 | League One · England |
| 1999-12-04 | Leyton OrientvCarlisleLeague Two · England | 0–1 | League Two · England |
| 1999-12-04 | VitessevAZ AlkmaarEredivisie · Netherlands | 0–2 | Eredivisie · Netherlands |