| 1999-04-05 | TranmerevOxfordChampionship · England | 2–2 | Championship · England |
| 1999-04-05 | Nott'm ForestvLiverpoolPremier League · England | 2–2 | Premier League · England |
| 1999-04-05 | Sheffield UnitedvWolvesChampionship · England | 1–1 | Championship · England |
| 1999-04-05 | BuryvBradfordChampionship · England | 0–2 | Championship · England |
| 1999-04-05 | MillwallvBlackpoolLeague One · England | 1–0 | League One · England |
| 1999-04-05 | IpswichvQPRChampionship · England | 3–1 | Championship · England |
| 1999-04-05 | MiddlesbroughvWimbledonPremier League · England | 3–1 | Premier League · England |
| 1999-04-05 | LincolnvNotts CountyLeague One · England | 0–1 | League One · England |
| 1999-04-04 | Ethnikos AsterasvAEKSuper League · Greece | 2–3 | Super League · Greece |
| 1999-04-04 | WattenscheidvDusseldorf2. Bundesliga · Germany | 2–0 | 2. Bundesliga · Germany |
| 1999-04-04 | PSV EindhovenvAjaxEredivisie · Netherlands | 3–1 | Eredivisie · Netherlands |
| 1999-04-04 | FC KolnvCottbus2. Bundesliga · Germany | 2–2 | 2. Bundesliga · Germany |
| 1999-04-04 | OFIvVeroiaSuper League · Greece | 3–0 | Super League · Greece |
| 1999-04-04 | UlmvGutersloh2. Bundesliga · Germany | 1–1 | 2. Bundesliga · Germany |
| 1999-04-04 | XanthivIonikosSuper League · Greece | 2–2 | Super League · Greece |
| 1999-04-04 | BetisvEspanolLa Liga · Spain | 0–1 | La Liga · Spain |
| 1999-04-04 | LeganesvOsasunaLa Liga 2 · Spain | 3–1 | La Liga 2 · Spain |
| 1999-04-04 | NAC BredavWillem IIEredivisie · Netherlands | 2–2 | Eredivisie · Netherlands |
| 1999-04-04 | FenerbahcevBesiktasSüper Lig · Turkey | 1–2 | Süper Lig · Turkey |
| 1999-04-04 | M'gladbachvHerthaBundesliga · Germany | 2–4 | Bundesliga · Germany |
| 1999-04-04 | ExtremaduravCeltaLa Liga · Spain | 1–1 | La Liga · Spain |
| 1999-04-04 | OurensevAlbaceteLa Liga 2 · Spain | 2–2 | La Liga 2 · Spain |
| 1999-04-04 | KocaelisporvGaziantepsporSüper Lig · Turkey | 1–1 | Süper Lig · Turkey |
| 1999-04-04 | ProodeytikivApollonSuper League · Greece | 0–1 | Super League · Greece |
| 1999-04-04 | OlympiakosvPAOKSuper League · Greece | 2–1 | Super League · Greece |
| 1999-04-04 | RecreativovBarcelona BLa Liga 2 · Spain | 5–0 | La Liga 2 · Spain |
| 1999-04-04 | IraklisvArisSuper League · Greece | 2–1 | Super League · Greece |
| 1999-04-04 | MalagavBadajozLa Liga 2 · Spain | 1–2 | La Liga 2 · Spain |
| 1999-04-04 | VallecanovAth Madrid BLa Liga 2 · Spain | 3–0 | La Liga 2 · Spain |
| 1999-04-04 | ValladolidvTenerifeLa Liga · Spain | 2–1 | La Liga · Spain |
| 1999-04-04 | VillarealvMallorcaLa Liga · Spain | 0–2 | La Liga · Spain |
| 1999-04-04 | Ethnikos PiraeusvKavalaSuper League · Greece | 0–2 | Super League · Greece |
| 1999-04-04 | BursasporvAltaySüper Lig · Turkey | 2–0 | Süper Lig · Turkey |
| 1999-04-04 | Ein FrankfurtvBochumBundesliga · Germany | 1–0 | Bundesliga · Germany |
| 1999-04-04 | KarabuksporvDardanelsporSüper Lig · Turkey | 1–0 | Süper Lig · Turkey |
| 1999-04-04 | BarcelonavOviedoLa Liga · Spain | 3–1 | La Liga · Spain |
| 1999-04-04 | ErzurumvAnkaragucuSüper Lig · Turkey | 2–2 | Süper Lig · Turkey |
| 1999-04-04 | NumanciavSp GijonLa Liga 2 · Spain | 1–1 | La Liga 2 · Spain |
| 1999-04-04 | Real MadridvAlavesLa Liga · Spain | 3–2 | La Liga · Spain |
| 1999-04-04 | St JohnstonevRangersPremiership · Scotland | 3–1 | Premiership · Scotland |
| 1999-04-04 | LogronesvMallorca BLa Liga 2 · Spain | 0–1 | La Liga 2 · Spain |
| 1999-04-04 | CompostelavEibarLa Liga 2 · Spain | 1–0 | La Liga 2 · Spain |
| 1999-04-04 | ZaragozavSalamancaLa Liga · Spain | 2–0 | La Liga · Spain |
| 1999-04-04 | LleidavLas PalmasLa Liga 2 · Spain | 1–1 | La Liga 2 · Spain |
| 1999-04-04 | GenclerbirligivSakaryasporSüper Lig · Turkey | 1–0 | Süper Lig · Turkey |
| 1999-04-04 | HannovervMainz2. Bundesliga · Germany | 3–2 | 2. Bundesliga · Germany |
| 1999-04-04 | PaniliakosvEleysinaSuper League · Greece | 2–0 | Super League · Greece |
| 1999-04-04 | Greuther FurthvUerdingen2. Bundesliga · Germany | 0–0 | 2. Bundesliga · Germany |
| 1999-04-04 | SevillavToledoLa Liga 2 · Spain | 2–2 | La Liga 2 · Spain |
| 1999-04-04 | Ath BilbaovSociedadLa Liga · Spain | 0–0 | La Liga · Spain |