| 1999-12-05 | BoavistavEst AmadoraPrimeira Liga · Portugal | 1–2 | Primeira Liga · Portugal |
| 1999-12-05 | BetisvEspanolLa Liga · Spain | 2–5 | La Liga · Spain |
| 1999-12-05 | F KolnvTB Berlin2. Bundesliga · Germany | 0–0 | 2. Bundesliga · Germany |
| 1999-12-05 | PanathinaikosvArisSuper League · Greece | 3–0 | Super League · Greece |
| 1999-12-05 | MalagavAth MadridLa Liga · Spain | 2–3 | La Liga · Spain |
| 1999-12-05 | MonzavSavoiaSerie B · Italy | 1–0 | Serie B · Italy |
| 1999-12-05 | FenerbahcevBursasporSüper Lig · Turkey | 2–2 | Süper Lig · Turkey |
| 1999-12-05 | HeartsvDundee UnitedPremiership · Scotland | 3–0 | Premiership · Scotland |
| 1999-12-05 | GentvMechelenPro League · Belgium | 6–1 | Pro League · Belgium |
| 1999-12-05 | Nott'm ForestvIpswichChampionship · England | 0–1 | Championship · England |
| 1999-12-05 | PanahaikivTrikalaSuper League · Greece | 3–0 | Super League · Greece |
| 1999-12-05 | VillarrealvOsasunaLa Liga 2 · Spain | 1–0 | La Liga 2 · Spain |
| 1999-12-05 | Sp GijonvMeridaLa Liga 2 · Spain | 1–2 | La Liga 2 · Spain |
| 1999-12-05 | GenoavFermanaSerie B · Italy | 1–1 | Serie B · Italy |
| 1999-12-05 | CosenzavSalernitanaSerie B · Italy | 0–0 | Serie B · Italy |
| 1999-12-05 | ParmavTorinoSerie A · Italy | 4–1 | Serie A · Italy |
| 1999-12-05 | AachenvSt Pauli2. Bundesliga · Germany | 3–1 | 2. Bundesliga · Germany |
| 1999-12-05 | ValladolidvSantanderLa Liga · Spain | 1–0 | La Liga · Spain |
| 1999-12-05 | StandardvAnderlechtPro League · Belgium | 0–0 | Pro League · Belgium |
| 1999-12-05 | BarivPiacenzaSerie A · Italy | 3–2 | Serie A · Italy |
| 1999-12-05 | AtalantavChievoSerie B · Italy | 0–1 | Serie B · Italy |
| 1999-12-05 | NurnbergvStuttgarter K2. Bundesliga · Germany | 3–2 | 2. Bundesliga · Germany |
| 1999-12-05 | La CorunavVallecanoLa Liga · Spain | 3–2 | La Liga · Spain |
| 1999-12-05 | DenizlisporvAnkaragucuSüper Lig · Turkey | 1–1 | Süper Lig · Turkey |
| 1999-12-05 | OFIvPAOKSuper League · Greece | 2–0 | Super League · Greece |
| 1999-12-05 | ExtremaduravSalamancaLa Liga 2 · Spain | 1–0 | La Liga 2 · Spain |
| 1999-12-05 | FiorentinavMilanSerie A · Italy | 2–1 | Serie A · Italy |
| 1999-12-05 | RomavLecceSerie A · Italy | 3–2 | Serie A · Italy |
| 1999-12-05 | Rio AvevGil VicentePrimeira Liga · Portugal | 3–1 | Primeira Liga · Portugal |
| 1999-12-05 | RecreativovToledoLa Liga 2 · Spain | 3–0 | La Liga 2 · Spain |
| 1999-12-05 | AjaxvWaalwijkEredivisie · Netherlands | 1–2 | Eredivisie · Netherlands |
| 1999-12-05 | PaniliakosvKalamataSuper League · Greece | 3–1 | Super League · Greece |
| 1999-12-05 | PanioniosvApollonSuper League · Greece | 3–1 | Super League · Greece |
| 1999-12-05 | SamsunsporvGoztepSüper Lig · Turkey | 4–0 | Süper Lig · Turkey |
| 1999-12-05 | AlavesvMallorcaLa Liga · Spain | 2–2 | La Liga · Spain |
| 1999-12-05 | Sp BragavSetubalPrimeira Liga · Portugal | 3–0 | Primeira Liga · Portugal |
| 1999-12-05 | GenkvHarelbekePro League · Belgium | 4–3 | Pro League · Belgium |
| 1999-12-05 | ElchevCompostelaLa Liga 2 · Spain | 1–1 | La Liga 2 · Spain |
| 1999-12-05 | KaiserslauternvWolfsburgBundesliga · Germany | 2–2 | Bundesliga · Germany |
| 1999-12-05 | MainzvBochum2. Bundesliga · Germany | 0–1 | 2. Bundesliga · Germany |
| 1999-12-05 | EibarvCordobaLa Liga 2 · Spain | 1–1 | La Liga 2 · Spain |
| 1999-12-05 | ProodeytikivKavalaSuper League · Greece | 1–1 | Super League · Greece |
| 1999-12-05 | UnterhachingvBielefeldBundesliga · Germany | 2–0 | Bundesliga · Germany |
| 1999-12-05 | ErzurumsporvAntalyasporSüper Lig · Turkey | 4–0 | Süper Lig · Turkey |
| 1999-12-05 | DerbyvLeedsPremier League · England | 0–1 | Premier League · England |
| 1999-12-05 | IntervUdineseSerie A · Italy | 3–0 | Serie A · Italy |
| 1999-12-05 | PescaravRavennaSerie B · Italy | 1–2 | Serie B · Italy |
| 1999-12-05 | AltayvIstanbulsporSüper Lig · Turkey | 0–0 | Süper Lig · Turkey |
| 1999-12-05 | LevantevLeganesLa Liga 2 · Spain | 5–2 | La Liga 2 · Spain |
| 1999-12-05 | VeneziavRegginaSerie A · Italy | 2–0 | Serie A · Italy |