| 1999-01-17 | Club BruggevSt TruidenPro League · Belgium | 3–2 | Pro League · Belgium |
| 1999-01-17 | ChievovMonzaSerie B · Italy | 3–2 | Serie B · Italy |
| 1999-01-17 | UdinesevEmpoliSerie A · Italy | 0–0 | Serie A · Italy |
| 1999-01-17 | ValenciavTenerifeLa Liga · Spain | 1–1 | La Liga · Spain |
| 1999-01-17 | KavalavVeroiaSuper League · Greece | 2–1 | Super League · Greece |
| 1999-01-17 | East FifevQueen of SthLeague One · Scotland | 0–1 | League One · Scotland |
| 1999-01-17 | GerminalvAalstPro League · Belgium | 1–0 | Pro League · Belgium |
| 1999-01-17 | SalamancavOviedoLa Liga · Spain | 1–1 | La Liga · Spain |
| 1999-01-17 | RomavVicenzaSerie A · Italy | 3–0 | Serie A · Italy |
| 1999-01-17 | BolognavInterSerie A · Italy | 2–0 | Serie A · Italy |
| 1999-01-17 | AlvercavCampomaiorensePrimeira Liga · Portugal | 2–1 | Primeira Liga · Portugal |
| 1999-01-17 | ApollonvEthnikos PiraeusSuper League · Greece | 4–0 | Super League · Greece |
| 1999-01-17 | RavennavCremoneseSerie B · Italy | 2–0 | Serie B · Italy |
| 1999-01-17 | TernanavRegginaSerie B · Italy | 0–0 | Serie B · Italy |
| 1999-01-17 | IonikosvPaniliakosSuper League · Greece | 1–1 | Super League · Greece |
| 1999-01-17 | Mallorca BvOsasunaLa Liga 2 · Spain | 1–1 | La Liga 2 · Spain |
| 1999-01-17 | Paris SGvNancyLigue 1 · France | 1–2 | Ligue 1 · France |
| 1999-01-17 | EibarvAlbaceteLa Liga 2 · Spain | 0–1 | La Liga 2 · Spain |
| 1999-01-17 | CosenzavLuccheseSerie B · Italy | 0–0 | Serie B · Italy |
| 1999-01-17 | ReggianavBresciaSerie B · Italy | 1–2 | Serie B · Italy |
| 1999-01-16 | Crystal PalacevStockportChampionship · England | 2–2 | Championship · England |
| 1999-01-16 | BarnsleyvBirminghamChampionship · England | 0–0 | Championship · England |
| 1999-01-16 | VallecanovLeganesLa Liga 2 · Spain | 1–0 | La Liga 2 · Spain |
| 1999-01-16 | WycombevMillwallLeague One · England | 0–1 | League One · England |
| 1999-01-16 | ShrewsburyvSouthendLeague Two · England | 3–1 | League Two · England |
| 1999-01-16 | ClydebankvSt MirrenChampionship · Scotland | 2–2 | Championship · Scotland |
| 1999-01-16 | PortsmouthvHuddersfieldChampionship · England | 1–0 | Championship · England |
| 1999-01-16 | CarlislevScunthorpeLeague Two · England | 0–1 | League Two · England |
| 1999-01-16 | BeverenvHarelbekePro League · Belgium | 0–3 | Pro League · Belgium |
| 1999-01-16 | Sheffield UnitedvBoltonChampionship · England | 1–2 | Championship · England |
| 1999-01-16 | ScarboroughvExeterLeague Two · England | 1–0 | League Two · England |
| 1999-01-16 | WolvesvWatfordChampionship · England | 0–0 | Championship · England |
| 1999-01-16 | LogronesvMeridaLa Liga 2 · Spain | 2–1 | La Liga 2 · Spain |
| 1999-01-16 | Lensv MonacoLigue 1 · France | 1–1 | Ligue 1 · France |
| 1999-01-16 | DerbyvBlackburnPremier League · England | 1–0 | Premier League · England |
| 1999-01-16 | ReadingvBristol RvsLeague One · England | 0–6 | League One · England |
| 1999-01-16 | NapolivVeronaSerie B · Italy | 0–0 | Serie B · Italy |
| 1999-01-16 | PeterborovCardiffLeague Two · England | 2–1 | League Two · England |
| 1999-01-16 | AmiensvGuingampLigue 2 · France | 1–0 | Ligue 2 · France |
| 1999-01-16 | AcademicavChavesPrimeira Liga · Portugal | 1–2 | Primeira Liga · Portugal |
| 1999-01-16 | GrimsbyvOxfordChampionship · England | 1–0 | Championship · England |
| 1999-01-16 | NantesvToulouseLigue 1 · France | 2–0 | Ligue 1 · France |
| 1999-01-16 | ChateaurouxvSedanLigue 2 · France | 1–0 | Ligue 2 · France |
| 1999-01-16 | AuxerrevLorientLigue 1 · France | 5–0 | Ligue 1 · France |
| 1999-01-16 | TottenhamvWimbledonPremier League · England | 0–0 | Premier League · England |
| 1999-01-16 | MontrosevDumbartonLeague Two · Scotland | 4–2 | League Two · Scotland |
| 1999-01-16 | OldhamvBlackpoolLeague One · England | 3–0 | League One · England |
| 1999-01-16 | West HamvSheffield WedsPremier League · England | 0–4 | Premier League · England |
| 1999-01-16 | LeicestervMan UnitedPremier League · England | 2–6 | Premier League · England |
| 1999-01-16 | FalkirkvMortonChampionship · Scotland | 1–2 | Championship · Scotland |