| 1999-01-30 | MouscronvLokerenPro League · Belgium | 5–1 | Pro League · Belgium |
| 1999-01-30 | FenerbahcevDardanelsporSüper Lig · Turkey | 3–1 | Süper Lig · Turkey |
| 1999-01-30 | LutonvBournemouthLeague One · England | 2–2 | League One · England |
| 1999-01-30 | IpswichvPort ValeChampionship · England | 1–0 | Championship · England |
| 1999-01-30 | VillarealvReal MadridLa Liga · Spain | 0–2 | La Liga · Spain |
| 1999-01-30 | MillwallvGillinghamLeague One · England | 3–3 | League One · England |
| 1999-01-30 | GenkvGentPro League · Belgium | 1–0 | Pro League · Belgium |
| 1999-01-30 | BetisvAlavesLa Liga · Spain | 1–0 | La Liga · Spain |
| 1999-01-30 | MansfieldvChesterLeague Two · England | 3–0 | League Two · England |
| 1999-01-30 | KocaelisporvSamsunsporSüper Lig · Turkey | 1–0 | Süper Lig · Turkey |
| 1999-01-30 | StenhousemuirvAlbion RvsLeague Two · Scotland | 1–2 | League Two · Scotland |
| 1999-01-30 | CardiffvBrentfordLeague Two · England | 4–1 | League Two · England |
| 1999-01-30 | WesterlovHarelbekePro League · Belgium | 0–3 | Pro League · Belgium |
| 1999-01-30 | Leyton OrientvDarlingtonLeague Two · England | 3–2 | League Two · England |
| 1999-01-30 | BoavistavCampomaiorensePrimeira Liga · Portugal | 2–1 | Primeira Liga · Portugal |
| 1999-01-30 | DumbartonvRoss CountyLeague Two · Scotland | 0–0 | League Two · Scotland |
| 1999-01-30 | ToulousevMetzLigue 1 · France | 1–0 | Ligue 1 · France |
| 1999-01-30 | Inverness CvForfarLeague One · Scotland | 2–0 | League One · Scotland |
| 1999-01-30 | Rio AvevSetubalPrimeira Liga · Portugal | 1–1 | Primeira Liga · Portugal |
| 1999-01-30 | LivingstonvPartickLeague One · Scotland | 1–1 | League One · Scotland |
| 1999-01-30 | NancyvMontpellierLigue 1 · France | 0–1 | Ligue 1 · France |
| 1999-01-30 | ChesterfieldvWycombeLeague One · England | 2–0 | League One · England |
| 1999-01-30 | SouthamptonvLeedsPremier League · England | 3–0 | Premier League · England |
| 1999-01-30 | MallorcavSalamancaLa Liga · Spain | 1–0 | La Liga · Spain |
| 1999-01-30 | HeartsvMotherwellPremiership · Scotland | 0–2 | Premiership · Scotland |
| 1999-01-30 | RecreativovCompostelaLa Liga 2 · Spain | 1–1 | La Liga 2 · Spain |
| 1999-01-30 | BlackburnvTottenhamPremier League · England | 1–1 | Premier League · England |
| 1999-01-30 | CharleroivOostendePro League · Belgium | 1–1 | Pro League · Belgium |
| 1999-01-30 | MortonvStranraerChampionship · Scotland | 1–0 | Championship · Scotland |
| 1999-01-30 | QPRvPortsmouthChampionship · England | 1–1 | Championship · England |
| 1999-01-30 | St MirrenvAyrChampionship · Scotland | 1–0 | Championship · Scotland |
| 1999-01-30 | WimbledonvWest HamPremier League · England | 0–0 | Premier League · England |
| 1999-01-30 | RochdalevHartlepoolLeague Two · England | 0–1 | League Two · England |
| 1999-01-30 | GuingampvAjaccioLigue 2 · France | 1–2 | Ligue 2 · France |
| 1999-01-30 | LorientvNantesLigue 1 · France | 1–1 | Ligue 1 · France |
| 1999-01-30 | HuddersfieldvBristol CityChampionship · England | 2–2 | Championship · England |
| 1999-01-30 | BoltonvNorwichChampionship · England | 2–0 | Championship · England |
| 1999-01-30 | BrightonvPeterboroLeague Two · England | 1–0 | League Two · England |
| 1999-01-30 | CannesvNiceLigue 2 · France | 0–1 | Ligue 2 · France |
| 1999-01-30 | HalifaxvRotherhamLeague Two · England | 2–4 | League Two · England |
| 1999-01-30 | ArbroathvClydeLeague One · Scotland | 0–3 | League One · Scotland |
| 1999-01-30 | CambridgevCarlisleLeague Two · England | 1–0 | League Two · England |
| 1999-01-30 | CoventryvLiverpoolPremier League · England | 2–1 | Premier League · England |
| 1999-01-30 | CowdenbeathvQueens ParkLeague Two · Scotland | 0–0 | League Two · Scotland |
| 1999-01-30 | StockportvWolvesChampionship · England | 1–2 | Championship · England |
| 1999-01-30 | ScunthorpevScarboroughLeague Two · England | 5–1 | League Two · England |
| 1999-01-30 | FulhamvNorthamptonLeague One · England | 2–0 | League One · England |
| 1999-01-30 | MiddlesbroughvLeicesterPremier League · England | 0–0 | Premier League · England |
| 1999-01-30 | SochauxvAuxerreLigue 1 · France | 1–1 | Ligue 1 · France |
| 1999-01-30 | Dundee UnitedvDunfermlinePremiership · Scotland | 1–1 | Premiership · Scotland |