| 1999-04-24 | HibernianvMortonChampionship · Scotland | 2–1 | Championship · Scotland |
| 1999-04-24 | NorthamptonvColchesterLeague One · England | 3–3 | League One · England |
| 1999-04-24 | LokerenvAalstPro League · Belgium | 6–2 | Pro League · Belgium |
| 1999-04-24 | East StirlingvCowdenbeathLeague Two · Scotland | 0–0 | League Two · Scotland |
| 1999-04-24 | Schalke 04vHamburgBundesliga · Germany | 1–4 | Bundesliga · Germany |
| 1999-04-24 | IpswichvCreweChampionship · England | 1–2 | Championship · England |
| 1999-04-24 | Est AmadoravAlvercaPrimeira Liga · Portugal | 1–0 | Primeira Liga · Portugal |
| 1999-04-24 | BlackburnvLiverpoolPremier League · England | 1–3 | Premier League · England |
| 1999-04-24 | LeicestervCoventryPremier League · England | 1–0 | Premier League · England |
| 1999-04-24 | ClydebankvAirdrieChampionship · Scotland | 0–1 | Championship · Scotland |
| 1999-04-24 | ForfarvAlloaLeague One · Scotland | 3–1 | League One · Scotland |
| 1999-04-24 | M'gladbachvWolfsburgBundesliga · Germany | 5–2 | Bundesliga · Germany |
| 1999-04-24 | Queen of SthvClydeLeague One · Scotland | 2–1 | League One · Scotland |
| 1999-04-24 | ScarboroughvCardiffLeague Two · England | 1–2 | League Two · England |
| 1999-04-24 | WiganvReadingLeague One · England | 4–1 | League One · England |
| 1999-04-24 |  Malawiv AngolaCOSAFA Cup qualification | 1–2 | COSAFA Cup qualification |
| 1999-04-24 | WatfordvCrystal PalaceChampionship · England | 2–1 | Championship · England |
| 1999-04-24 | DundeevKilmarnockPremiership · Scotland | 2–1 | Premiership · Scotland |
| 1999-04-24 | Queens ParkvBrechinLeague Two · Scotland | 0–2 | League Two · Scotland |
| 1999-04-24 | StokevBurnleyLeague One · England | 1–4 | League One · England |
| 1999-04-24 | NiortvCannesLigue 2 · France | 3–2 | Ligue 2 · France |
| 1999-04-24 | MansfieldvHartlepoolLeague Two · England | 2–0 | League Two · England |
| 1999-04-24 | LavalvSt EtienneLigue 2 · France | 1–1 | Ligue 2 · France |
| 1999-04-24 | ChestervHalifaxLeague Two · England | 2–2 | League Two · England |
| 1999-04-24 | HamiltonvRaith RvsChampionship · Scotland | 1–2 | Championship · Scotland |
| 1999-04-24 | SouthendvBrentfordLeague Two · England | 1–4 | League Two · England |
| 1999-04-24 | PaniliakosvOFISuper League · Greece | 1–2 | Super League · Greece |
| 1999-04-24 | TranmerevPort ValeChampionship · England | 1–1 | Championship · England |
| 1999-04-24 | SochauxvBordeauxLigue 1 · France | 2–0 | Ligue 1 · France |
| 1999-04-24 | OldhamvGillinghamLeague One · England | 1–4 | League One · England |
| 1999-04-24 | OxfordvNorwichChampionship · England | 2–4 | Championship · England |
| 1999-04-24 | BlackpoolvBristol RvsLeague One · England | 1–2 | League One · England |
| 1999-04-24 | East FifevArbroathLeague One · Scotland | 1–2 | League One · Scotland |
| 1999-04-24 | AjacciovLilleLigue 2 · France | 0–2 | Ligue 2 · France |
| 1999-04-24 | Aston VillavNott'm ForestPremier League · England | 2–0 | Premier League · England |
| 1999-04-24 | CaenvLe MansLigue 2 · France | 3–2 | Ligue 2 · France |
| 1999-04-24 | LommelvStandardPro League · Belgium | 3–0 | Pro League · Belgium |
| 1999-04-24 | NantesvMetzLigue 1 · France | 0–0 | Ligue 1 · France |
| 1999-04-24 | Leyton OrientvShrewsburyLeague Two · England | 6–1 | League Two · England |
| 1999-04-24 | SedanvNimesLigue 2 · France | 1–1 | Ligue 2 · France |
| 1999-04-24 | ChateaurouxvRed Star 93Ligue 2 · France | 1–4 | Ligue 2 · France |
| 1999-04-24 | SwindonvGrimsbyChampionship · England | 2–0 | Championship · England |
| 1999-04-24 | St MirrenvStranraerChampionship · Scotland | 5–1 | Championship · Scotland |
| 1999-04-24 | St JohnstonevCelticPremiership · Scotland | 1–0 | Premiership · Scotland |
| 1999-04-24 | Bristol CityvBirminghamChampionship · England | 1–2 | Championship · England |
| 1999-04-24 | FulhamvWrexhamLeague One · England | 1–1 | League One · England |
| 1999-04-24 | AmiensvNiceLigue 2 · France | 0–1 | Ligue 2 · France |
| 1999-04-24 | Albion RvsvBerwickLeague Two · Scotland | 0–3 | League Two · Scotland |
| 1999-04-24 | TottenhamvWest HamPremier League · England | 1–2 | Premier League · England |
| 1999-04-24 |  MonacovBastiaLigue 1 · France | 1–1 | Ligue 1 · France |