| 1999-01-31 | MilanvSalernitanaSerie A · Italy | 3–2 | Serie A · Italy |
| 1999-01-31 | CosenzavNapoliSerie B · Italy | 1–0 | Serie B · Italy |
| 1999-01-31 | FiorentinavVicenzaSerie A · Italy | 3–0 | Serie A · Italy |
| 1999-01-31 | BadajozvLogronesLa Liga 2 · Spain | 2–1 | La Liga 2 · Spain |
| 1999-01-31 | AEKvOlympiakosSuper League · Greece | 2–0 | Super League · Greece |
| 1999-01-31 | KarabuksporvBursasporSüper Lig · Turkey | 1–0 | Süper Lig · Turkey |
| 1999-01-31 | UdinesevBolognaSerie A · Italy | 2–0 | Serie A · Italy |
| 1999-01-31 | AltayvGalatasaraySüper Lig · Turkey | 0–2 | Süper Lig · Turkey |
| 1999-01-31 | CelticvSt JohnstonePremiership · Scotland | 5–0 | Premiership · Scotland |
| 1999-01-31 | ErzurumvGenclerbirligiSüper Lig · Turkey | 2–2 | Süper Lig · Turkey |
| 1999-01-31 | La CorunavCeltaLa Liga · Spain | 2–1 | La Liga · Spain |
| 1999-01-31 | CesenavBresciaSerie B · Italy | 1–0 | Serie B · Italy |
| 1999-01-31 | BarivLazioSerie A · Italy | 1–3 | Serie A · Italy |
| 1999-01-31 | PerugiavSampdoriaSerie A · Italy | 2–0 | Serie A · Italy |
| 1999-01-31 | RegginavLecceSerie B · Italy | 1–3 | Serie B · Italy |
| 1999-01-31 | MeridavNumanciaLa Liga 2 · Spain | 2–0 | La Liga 2 · Spain |
| 1999-01-31 | ToledovSp GijonLa Liga 2 · Spain | 2–5 | La Liga 2 · Spain |
| 1999-01-31 | GenoavAtalantaSerie B · Italy | 2–1 | Serie B · Italy |
| 1999-01-31 | PiacenzavInterSerie A · Italy | 0–0 | Serie A · Italy |
| 1999-01-31 | ArsenalvChelseaPremier League · England | 1–0 | Premier League · England |
| 1999-01-31 | PanioniosvPAOKSuper League · Greece | 0–1 | Super League · Greece |
| 1999-01-31 | OsasunavVallecanoLa Liga 2 · Spain | 1–1 | La Liga 2 · Spain |
| 1999-01-31 | LucchesevMonzaSerie B · Italy | 1–2 | Serie B · Italy |
| 1999-01-31 | AlvercavLeiriaPrimeira Liga · Portugal | 0–2 | Primeira Liga · Portugal |
| 1999-01-31 | VeroiavEthnikos PiraeusSuper League · Greece | 4–3 | Super League · Greece |
| 1999-01-31 | Est AmadoravChavesPrimeira Liga · Portugal | 2–1 | Primeira Liga · Portugal |
| 1999-01-31 | RomavEmpoliSerie A · Italy | 1–1 | Serie A · Italy |
| 1999-01-31 | HerculesvAth Madrid BLa Liga 2 · Spain | 1–3 | La Liga 2 · Spain |
| 1999-01-31 | BirminghamvBradfordChampionship · England | 2–1 | Championship · England |
| 1999-01-31 | CharltonvMan UnitedPremier League · England | 0–1 | Premier League · England |
| 1999-01-31 | AlbacetevLas PalmasLa Liga 2 · Spain | 1–0 | La Liga 2 · Spain |
| 1999-01-30 | HamiltonvFalkirkChampionship · Scotland | 0–2 | Championship · Scotland |
| 1999-01-30 | SouthendvTorquayLeague Two · England | 0–0 | League Two · England |
| 1999-01-30 | West BromvGrimsbyChampionship · England | 1–1 | Championship · England |
| 1999-01-30 | NewcastlevAston VillaPremier League · England | 2–1 | Premier League · England |
| 1999-01-30 | Notts CountyvReadingLeague One · England | 1–1 | League One · England |
| 1999-01-30 | HullvShrewsburyLeague Two · England | 1–1 | League Two · England |
| 1999-01-30 | Le MansvLilleLigue 2 · France | 2–1 | Ligue 2 · France |
| 1999-01-30 | EibarvMalagaLa Liga 2 · Spain | 0–0 | La Liga 2 · Spain |
| 1999-01-30 | Raith RvsvClydebankChampionship · Scotland | 2–1 | Championship · Scotland |
| 1999-01-30 | AberdeenvRangersPremiership · Scotland | 2–4 | Premiership · Scotland |
| 1999-01-30 | LensvLyonLigue 1 · France | 0–3 | Ligue 1 · France |
| 1999-01-30 | BeauvaisvSt EtienneLigue 2 · France | 1–2 | Ligue 2 · France |
| 1999-01-30 | Ath MadridvValenciaLa Liga · Spain | 1–2 | La Liga · Spain |
| 1999-01-30 | TroyesvGueugnonLigue 2 · France | 0–0 | Ligue 2 · France |
| 1999-01-30 | FarensevPortoPrimeira Liga · Portugal | 0–3 | Primeira Liga · Portugal |
| 1999-01-30 | EvertonvNott'm ForestPremier League · England | 0–1 | Premier League · England |
| 1999-01-30 | StirlingvEast FifeLeague One · Scotland | 0–1 | League One · Scotland |
| 1999-01-30 | BeverenvLiersePro League · Belgium | 1–3 | Pro League · Belgium |
| 1999-01-30 | LeganesvLleidaLa Liga 2 · Spain | 1–0 | La Liga 2 · Spain |