| 1999-01-09 | Sheffield WedsvTottenhamPremier League · England | 0–0 | Premier League · England |
| 1999-01-09 | CrewevNorwichChampionship · England | 3–2 | Championship · England |
| 1999-01-09 | MillwallvWiganLeague One · England | 3–1 | League One · England |
| 1999-01-09 | St MirrenvHibernianChampionship · Scotland | 1–2 | Championship · Scotland |
| 1999-01-09 | West BromvBarnsleyChampionship · England | 2–0 | Championship · England |
| 1999-01-09 | QPRvSunderlandChampionship · England | 2–2 | Championship · England |
| 1999-01-09 | Inverness CvArbroathLeague One · Scotland | 2–0 | League One · Scotland |
| 1999-01-09 | Notts CountyvOldhamLeague One · England | 0–1 | League One · England |
| 1999-01-09 | SwindonvSheffield UnitedChampionship · England | 2–2 | Championship · England |
| 1999-01-09 | CoventryvNott'm ForestPremier League · England | 4–0 | Premier League · England |
| 1999-01-09 | Raith RvsvFalkirkChampionship · Scotland | 2–1 | Championship · Scotland |
| 1999-01-09 | BrightonvCarlisleLeague Two · England | 1–3 | League Two · England |
| 1999-01-09 | NewcastlevChelseaPremier League · England | 0–1 | Premier League · England |
| 1999-01-09 | StokevNorthamptonLeague One · England | 3–1 | League One · England |
| 1999-01-09 | Barcelona BvEibarLa Liga 2 · Spain | 0–0 | La Liga 2 · Spain |
| 1999-01-09 | CardiffvHartlepoolLeague Two · England | 4–1 | League Two · England |
| 1999-01-09 | BlackburnvLeedsPremier League · England | 1–0 | Premier League · England |
| 1999-01-09 | StranraervHamiltonChampionship · Scotland | 2–2 | Championship · Scotland |
| 1999-01-09 | MansfieldvBrentfordLeague Two · England | 3–1 | League Two · England |
| 1999-01-09 | WimbledonvDerbyPremier League · England | 2–1 | Premier League · England |
| 1999-01-09 | YorkvPrestonLeague One · England | 0–1 | League One · England |
| 1999-01-09 | Leyton OrientvChesterLeague Two · England | 2–2 | League Two · England |
| 1999-01-09 | LeganesvAth Madrid BLa Liga 2 · Spain | 1–1 | La Liga 2 · Spain |
| 1999-01-09 | SouthamptonvCharltonPremier League · England | 3–1 | Premier League · England |
| 1999-01-09 | MiddlesbroughvAston VillaPremier League · England | 0–0 | Premier League · England |
| 1999-01-09 | RecreativovLogronesLa Liga 2 · Spain | 1–2 | La Liga 2 · Spain |
| 1999-01-09 | CambridgevTorquayLeague Two · England | 2–0 | League Two · England |
| 1999-01-09 | MontrosevAlbion RvsLeague Two · Scotland | 2–3 | League Two · Scotland |
| 1999-01-09 | OurensevLleidaLa Liga 2 · Spain | 1–1 | La Liga 2 · Spain |
| 1999-01-09 | ScunthorpevShrewsburyLeague Two · England | 3–0 | League Two · England |
| 1999-01-09 | BlackpoolvMan CityLeague One · England | 0–0 | League One · England |
| 1999-01-09 | WatfordvPortsmouthChampionship · England | 0–0 | Championship · England |
| 1999-01-09 | OxfordvBristol CityChampionship · England | 0–0 | Championship · England |
| 1999-01-09 | FulhamvMacclesfieldLeague One · England | 1–0 | League One · England |
| 1999-01-09 | ReadingvWrexhamLeague One · England | 4–0 | League One · England |
| 1999-01-09 | BarcelonavAth BilbaoLa Liga · Spain | 4–2 | La Liga · Spain |
| 1999-01-09 | HullvRotherhamLeague Two · England | 1–0 | League Two · England |
| 1999-01-09 | ArsenalvLiverpoolPremier League · England | 0–0 | Premier League · England |
| 1999-01-09 | BarnetvDarlingtonLeague Two · England | 3–0 | League Two · England |
| 1999-01-09 | WalsallvGillinghamLeague One · England | 2–1 | League One · England |
| 1999-01-09 | IpswichvGrimsbyChampionship · England | 0–1 | Championship · England |
| 1999-01-09 | RochdalevPlymouthLeague Two · England | 1–1 | League Two · England |
| 1999-01-09 | StockportvBradfordChampionship · England | 1–2 | Championship · England |
| 1999-01-09 | SouthendvScarboroughLeague Two · England | 1–0 | League Two · England |
| 1999-01-09 | BresciavTorinoSerie B · Italy | 2–1 | Serie B · Italy |
| 1999-01-08 | TranmerevWolvesChampionship · England | 1–2 | Championship · England |
| 1999-01-06 | PescaravF. AndriaSerie B · Italy | 2–1 | Serie B · Italy |
| 1999-01-06 | TorinovTrevisoSerie B · Italy | 0–0 | Serie B · Italy |
| 1999-01-06 | BarivPerugiaSerie A · Italy | 2–1 | Serie A · Italy |
| 1999-01-06 | AtalantavLecceSerie B · Italy | 2–1 | Serie B · Italy |