| 1999-01-24 |  Guineav MoroccoAfrican Cup of Nations qualification | 1–1 | African Cup of Nations qualification |
| 1999-01-24 |  Ivory Coastv NamibiaAfrican Cup of Nations qualification | 3–0 | African Cup of Nations qualification |
| 1999-01-24 | CesenavCosenzaSerie B · Italy | 3–0 | Serie B · Italy |
| 1999-01-24 | SevillavMalagaLa Liga 2 · Spain | 2–3 | La Liga 2 · Spain |
| 1999-01-24 | SampdoriavUdineseSerie A · Italy | 1–1 | Serie A · Italy |
| 1999-01-24 | SalgueirosvMaritimoPrimeira Liga · Portugal | 2–2 | Primeira Liga · Portugal |
| 1999-01-24 | VeroiavPanathinaikosSuper League · Greece | 0–1 | Super League · Greece |
| 1999-01-24 | CampomaiorensevAcademicaPrimeira Liga · Portugal | 2–1 | Primeira Liga · Portugal |
| 1999-01-24 | VeronavGenoaSerie B · Italy | 2–1 | Serie B · Italy |
| 1999-01-24 | ValladolidvSantanderLa Liga · Spain | 0–0 | La Liga · Spain |
| 1999-01-24 | OlympiakosvPanioniosSuper League · Greece | 5–0 | Super League · Greece |
| 1999-01-23 | LeganesvLogronesLa Liga 2 · Spain | 1–1 | La Liga 2 · Spain |
| 1999-01-23 | St TruidenvGerminalPro League · Belgium | 2–0 | Pro League · Belgium |
| 1999-01-23 | MonzavAtalantaSerie B · Italy | 1–2 | Serie B · Italy |
| 1999-01-23 | YorkvReadingLeague One · England | 1–1 | League One · England |
| 1999-01-23 | AnderlechtvWesterloPro League · Belgium | 3–2 | Pro League · Belgium |
| 1999-01-23 | Barcelona BvLas PalmasLa Liga 2 · Spain | 1–2 | La Liga 2 · Spain |
| 1999-01-23 | LincolnvNorthamptonLeague One · England | 1–0 | League One · England |
| 1999-01-23 | LommelvClub BruggePro League · Belgium | 2–1 | Pro League · Belgium |
| 1999-01-23 |  Zimbabwev MalawiFriendly | 3–0 | Friendly |
| 1999-01-23 | BoavistavAlvercaPrimeira Liga · Portugal | 3–0 | Primeira Liga · Portugal |
| 1999-01-23 | HalifaxvPlymouthLeague Two · England | 2–0 | League Two · England |
| 1999-01-23 | WatfordvWest BromChampionship · England | 0–2 | Championship · England |
| 1999-01-23 | BenficavRio AvePrimeira Liga · Portugal | 3–1 | Primeira Liga · Portugal |
| 1999-01-23 |  Senegalv Burkina FasoAfrican Cup of Nations qualification | 1–1 | African Cup of Nations qualification |
| 1999-01-23 | StokevColchesterLeague One · England | 3–3 | League One · England |
| 1999-01-23 | ExetervPeterboroLeague Two · England | 2–0 | League Two · England |
| 1999-01-23 |  Eritreav CameroonAfrican Cup of Nations qualification | 0–0 | African Cup of Nations qualification |
| 1999-01-23 | LutonvWiganLeague One · England | 0–4 | League One · England |
| 1999-01-23 | LokerenvBeverenPro League · Belgium | 4–3 | Pro League · Belgium |
| 1999-01-23 | AnkaragucuvGalatasaraySüper Lig · Turkey | 2–2 | Süper Lig · Turkey |
| 1999-01-23 | SouthendvCarlisleLeague Two · England | 0–1 | League Two · England |
| 1999-01-23 | CambridgevChesterLeague Two · England | 2–1 | League Two · England |
| 1999-01-23 | BrightonvScarboroughLeague Two · England | 1–0 | League Two · England |
| 1999-01-23 | HullvHartlepoolLeague Two · England | 4–0 | League Two · England |
| 1999-01-23 | LiersevCharleroiPro League · Belgium | 4–0 | Pro League · Belgium |
| 1999-01-23 | OostendevKortrijkPro League · Belgium | 1–3 | Pro League · Belgium |
| 1999-01-23 | ChesterfieldvPrestonLeague One · England | 0–1 | League One · England |
| 1999-01-23 |  Mauritiusv South AfricaAfrican Cup of Nations qualification | 1–1 | African Cup of Nations qualification |
| 1999-01-23 | RochdalevBrentfordLeague Two · England | 2–0 | League Two · England |
| 1999-01-23 | Ath BilbaovBetisLa Liga · Spain | 0–0 | La Liga · Spain |
| 1999-01-23 | WalsallvMan CityLeague One · England | 1–1 | League One · England |
| 1999-01-23 | MillwallvBurnleyLeague One · England | 1–2 | League One · England |
| 1999-01-23 | OurensevCompostelaLa Liga 2 · Spain | 0–2 | La Liga 2 · Spain |
| 1999-01-23 | BarnetvShrewsburyLeague Two · England | 2–2 | League Two · England |
| 1999-01-23 | CardiffvDarlingtonLeague Two · England | 3–2 | League Two · England |
| 1999-01-23 | ChavesvSp LisbonPrimeira Liga · Portugal | 2–2 | Primeira Liga · Portugal |
| 1999-01-22 |  Estoniav NorwayFriendly | 3–3 | Friendly |
| 1999-01-22 | LeiriavGuimaraesPrimeira Liga · Portugal | 0–1 | Primeira Liga · Portugal |
| 1999-01-22 | MansfieldvRotherhamLeague Two · England | 0–3 | League Two · England |