| 1999-02-27 | West HamvBlackburnPremier League · England | 2–0 | Premier League · England |
| 1999-02-27 | LincolnvBristol RvsLeague One · England | 1–0 | League One · England |
| 1999-02-27 | BrentfordvScarboroughLeague Two · England | 1–1 | League Two · England |
| 1999-02-27 | IstanbulsporvTrabzonsporSüper Lig · Turkey | 0–0 | Süper Lig · Turkey |
| 1999-02-27 | ShrewsburyvDarlingtonLeague Two · England | 3–0 | League Two · England |
| 1999-02-27 | St MirrenvHamiltonChampionship · Scotland | 1–0 | Championship · Scotland |
| 1999-02-27 | BeverenvStandardPro League · Belgium | 0–6 | Pro League · Belgium |
| 1999-02-27 | DundeevSt JohnstonePremiership · Scotland | 0–1 | Premiership · Scotland |
| 1999-02-27 | Ath MadridvOviedoLa Liga · Spain | 0–0 | La Liga · Spain |
| 1999-02-27 | OsasunavCompostelaLa Liga 2 · Spain | 2–1 | La Liga 2 · Spain |
| 1999-02-27 | FreiburgvWolfsburgBundesliga · Germany | 0–0 | Bundesliga · Germany |
| 1999-02-27 | BetisvReal MadridLa Liga · Spain | 3–2 | La Liga · Spain |
| 1999-02-27 | ValencevLe MansLigue 2 · France | 0–1 | Ligue 2 · France |
| 1999-02-27 | LillevRed Star 93Ligue 2 · France | 2–0 | Ligue 2 · France |
| 1999-02-27 | OxfordvSunderlandChampionship · England | 0–0 | Championship · England |
| 1999-02-27 | StirlingvClydeLeague One · Scotland | 2–3 | League One · Scotland |
| 1999-02-27 | LutonvBlackpoolLeague One · England | 1–0 | League One · England |
| 1999-02-27 | AmiensvGueugnonLigue 2 · France | 1–0 | Ligue 2 · France |
| 1999-02-27 | MotherwellvDunfermlinePremiership · Scotland | 1–1 | Premiership · Scotland |
| 1999-02-27 | East FifevAlloaLeague One · Scotland | 0–4 | League One · Scotland |
| 1999-02-27 | Roda JCvAZ AlkmaarEredivisie · Netherlands | 8–2 | Eredivisie · Netherlands |
| 1999-02-27 | CharltonvNott'm ForestPremier League · England | 0–0 | Premier League · England |
| 1999-02-27 | Beira MarvSp LisbonPrimeira Liga · Portugal | 2–2 | Primeira Liga · Portugal |
| 1999-02-27 | StenhousemuirvCowdenbeathLeague Two · Scotland | 4–1 | League Two · Scotland |
| 1999-02-27 | Barcelona BvLleidaLa Liga 2 · Spain | 1–2 | La Liga 2 · Spain |
| 1999-02-27 | Inverness CvLivingstonLeague One · Scotland | 3–1 | League One · Scotland |
| 1999-02-27 | YorkvFulhamLeague One · England | 0–3 | League One · England |
| 1999-02-27 | NorwichvSheffield UnitedChampionship · England | 1–1 | Championship · England |
| 1999-02-27 | ColchestervReadingLeague One · England | 1–1 | League One · England |
| 1999-02-27 | Bristol CityvIpswichChampionship · England | 0–1 | Championship · England |
| 1999-02-27 | BradfordvWest BromChampionship · England | 1–0 | Championship · England |
| 1999-02-27 | KilmarnockvRangersPremiership · Scotland | 0–5 | Premiership · Scotland |
| 1999-02-27 | GuingampvCaenLigue 2 · France | 0–0 | Ligue 2 · France |
| 1999-02-27 | ChestervCarlisleLeague Two · England | 2–1 | League Two · England |
| 1999-02-27 | PiacenzavBolognaSerie A · Italy | 5–0 | Serie A · Italy |
| 1999-02-27 | Sheffield WedsvMiddlesbroughPremier League · England | 3–1 | Premier League · England |
| 1999-02-27 | HalifaxvHullLeague Two · England | 0–1 | League Two · England |
| 1999-02-27 | BursasporvBesiktasSüper Lig · Turkey | 1–2 | Süper Lig · Turkey |
| 1999-02-27 | BoltonvCreweChampionship · England | 1–3 | Championship · England |
| 1999-02-27 | AjacciovBeauvaisLigue 2 · France | 2–1 | Ligue 2 · France |
| 1999-02-27 | Munich 1860vDuisburgBundesliga · Germany | 0–0 | Bundesliga · Germany |
| 1999-02-27 | LavalvCannesLigue 2 · France | 1–2 | Ligue 2 · France |
| 1999-02-27 | Notts CountyvWalsallLeague One · England | 2–1 | League One · England |
| 1999-02-27 | RomavMilanSerie A · Italy | 1–0 | Serie A · Italy |
| 1999-02-27 | HartlepoolvRotherhamLeague Two · England | 0–0 | League Two · England |
| 1999-02-27 | CambridgevSouthendLeague Two · England | 3–0 | League Two · England |
| 1999-02-27 | NijmegenvMVV MaastrichtEredivisie · Netherlands | 1–1 | Eredivisie · Netherlands |
| 1999-02-27 | EvertonvWimbledonPremier League · England | 1–1 | Premier League · England |
| 1999-02-27 | Queen of SthvArbroathLeague One · Scotland | 3–0 | League One · Scotland |
| 1999-02-27 | BarcelonavValenciaLa Liga · Spain | 2–4 | La Liga · Spain |