| 1999-12-21 | MVV MaastrichtvPSV EindhovenEredivisie · Netherlands | 0–2 | Eredivisie · Netherlands |
| 1999-12-20 | PortovFarensePrimeira Liga · Portugal | 5–0 | Primeira Liga · Portugal |
| 1999-12-20 | M'gladbachvNurnberg2. Bundesliga · Germany | 4–0 | 2. Bundesliga · Germany |
| 1999-12-20 | NapolivCesenaSerie B · Italy | 1–1 | Serie B · Italy |
| 1999-12-19 |  Dominicav Saint LuciaFriendly | 2–1 | Friendly |
| 1999-12-19 | MonzavSampdoriaSerie B · Italy | 1–1 | Serie B · Italy |
| 1999-12-19 | CampomaiorensevSetubalPrimeira Liga · Portugal | 0–1 | Primeira Liga · Portugal |
| 1999-12-19 | GetafevLleidaLa Liga 2 · Spain | 2–1 | La Liga 2 · Spain |
| 1999-12-19 | GuimaraesvBenficaPrimeira Liga · Portugal | 2–1 | Primeira Liga · Portugal |
| 1999-12-19 | LeiriavSalgueirosPrimeira Liga · Portugal | 1–4 | Primeira Liga · Portugal |
| 1999-12-19 | ToledovMeridaLa Liga 2 · Spain | 3–0 | La Liga 2 · Spain |
| 1999-12-19 | BesiktasvAntalyasporSüper Lig · Turkey | 4–0 | Süper Lig · Turkey |
| 1999-12-19 | LaziovPiacenzaSerie A · Italy | 2–0 | Serie A · Italy |
| 1999-12-19 | AltayvTrabzonsporSüper Lig · Turkey | 3–1 | Süper Lig · Turkey |
| 1999-12-19 | TorinovUdineseSerie A · Italy | 0–1 | Serie A · Italy |
| 1999-12-19 | HeartsvHibernianPremiership · Scotland | 0–3 | Premiership · Scotland |
| 1999-12-19 | AtalantavAlzanoSerie B · Italy | 1–0 | Serie B · Italy |
| 1999-12-19 | IstanbulsporvGaziantepsporSüper Lig · Turkey | 1–1 | Süper Lig · Turkey |
| 1999-12-19 | UtrechtvFeyenoordEredivisie · Netherlands | 3–4 | Eredivisie · Netherlands |
| 1999-12-19 | FiorentinavJuventusSerie A · Italy | 1–1 | Serie A · Italy |
| 1999-12-19 | Rio AvevBoavistaPrimeira Liga · Portugal | 2–1 | Primeira Liga · Portugal |
| 1999-12-19 | BelenensesvSanta ClaraPrimeira Liga · Portugal | 3–1 | Primeira Liga · Portugal |
| 1999-12-19 | RavennavFermanaSerie B · Italy | 1–0 | Serie B · Italy |
| 1999-12-19 | GraafschapvAjaxEredivisie · Netherlands | 1–1 | Eredivisie · Netherlands |
| 1999-12-19 | VansporvAdanasporSüper Lig · Turkey | 0–2 | Süper Lig · Turkey |
| 1999-12-19 | ErzurumsporvGoztepSüper Lig · Turkey | 0–0 | Süper Lig · Turkey |
| 1999-12-19 | Hansa RostockvSchalke 04Bundesliga · Germany | 1–0 | Bundesliga · Germany |
| 1999-12-19 | DortmundvHerthaBundesliga · Germany | 4–0 | Bundesliga · Germany |
| 1999-12-19 | PerugiavBolognaSerie A · Italy | 3–2 | Serie A · Italy |
| 1999-12-19 | MalagavSociedadLa Liga · Spain | 0–0 | La Liga · Spain |
| 1999-12-19 | VillarrealvCordobaLa Liga 2 · Spain | 2–1 | La Liga 2 · Spain |
| 1999-12-19 | BarcelonavAth MadridLa Liga · Spain | 2–1 | La Liga · Spain |
| 1999-12-19 | Ath BilbaovZaragozaLa Liga · Spain | 2–2 | La Liga · Spain |
| 1999-12-19 | TernanavEmpoliSerie B · Italy | 1–1 | Serie B · Italy |
| 1999-12-19 | NumanciavSantanderLa Liga · Spain | 2–1 | La Liga · Spain |
| 1999-12-19 | MilanvRegginaSerie A · Italy | 2–2 | Serie A · Italy |
| 1999-12-19 | TrevisovBresciaSerie B · Italy | 1–1 | Serie B · Italy |
| 1999-12-19 | ChelseavLeedsPremier League · England | 0–2 | Premier League · England |
| 1999-12-19 | LevantevCompostelaLa Liga 2 · Spain | 0–0 | La Liga 2 · Spain |
| 1999-12-19 | TenerifevOsasunaLa Liga 2 · Spain | 1–1 | La Liga 2 · Spain |
| 1999-12-19 | OberhausenvSt Pauli2. Bundesliga · Germany | 2–2 | 2. Bundesliga · Germany |
| 1999-12-19 | GenoavSavoiaSerie B · Italy | 1–0 | Serie B · Italy |
| 1999-12-19 | RecreativovAth Madrid BLa Liga 2 · Spain | 1–2 | La Liga 2 · Spain |
| 1999-12-19 | BetisvMallorcaLa Liga · Spain | 1–0 | La Liga · Spain |
| 1999-12-19 | OviedovSevillaLa Liga · Spain | 4–2 | La Liga · Spain |
| 1999-12-19 | PescaravSalernitanaSerie B · Italy | 2–2 | Serie B · Italy |
| 1999-12-19 | OffenbachvF Koln2. Bundesliga · Germany | 4–3 | 2. Bundesliga · Germany |
| 1999-12-19 | ElchevLas PalmasLa Liga 2 · Spain | 0–3 | La Liga 2 · Spain |
| 1999-12-19 | AlvercavGil VicentePrimeira Liga · Portugal | 4–2 | Primeira Liga · Portugal |
| 1999-12-19 | Sp GijonvLeganesLa Liga 2 · Spain | 3–0 | La Liga 2 · Spain |