| 1999-12-26 | SouthendvNorthamptonLeague Two · England | 2–2 | League Two · England |
| 1999-12-26 | West BromvMan CityChampionship · England | 0–2 | Championship · England |
| 1999-12-26 | CoventryvArsenalPremier League · England | 3–2 | Premier League · England |
| 1999-12-26 | GaziantepsporvSamsunsporSüper Lig · Turkey | 5–2 | Süper Lig · Turkey |
| 1999-12-26 | CarlislevRochdaleLeague Two · England | 1–2 | League Two · England |
| 1999-12-26 | LutonvChesterfieldLeague One · England | 1–1 | League One · England |
| 1999-12-26 | DerbyvAston VillaPremier League · England | 0–2 | Premier League · England |
| 1999-12-26 | WalsallvTranmereChampionship · England | 1–2 | Championship · England |
| 1999-12-26 | WimbledonvWest HamPremier League · England | 2–2 | Premier League · England |
| 1999-12-26 | NorwichvQPRChampionship · England | 2–1 | Championship · England |
| 1999-12-26 | WycombevBournemouthLeague One · England | 2–1 | League One · England |
| 1999-12-26 | FulhamvIpswichChampionship · England | 0–0 | Championship · England |
| 1999-12-26 | BlackburnvNott'm ForestChampionship · England | 2–1 | Championship · England |
| 1999-12-26 | NewcastlevLiverpoolPremier League · England | 2–2 | Premier League · England |
| 1999-12-26 | GoztepvGenclerbirligiSüper Lig · Turkey | 3–2 | Süper Lig · Turkey |
| 1999-12-26 | GrimsbyvBarnsleyChampionship · England | 0–3 | Championship · England |
| 1999-12-26 | PlymouthvTorquayLeague Two · England | 2–2 | League Two · England |
| 1999-12-26 | GillinghamvColchesterLeague One · England | 2–1 | League One · England |
| 1999-12-26 | WrexhamvPrestonLeague One · England | 0–0 | League One · England |
| 1999-12-26 | CharltonvCrystal PalaceChampionship · England | 2–1 | Championship · England |
| 1999-12-25 | AnkaragucuvAltaySüper Lig · Turkey | 3–0 | Süper Lig · Turkey |
| 1999-12-25 | AntalyasporvDenizlisporSüper Lig · Turkey | 2–2 | Süper Lig · Turkey |
| 1999-12-25 | AdanasporvKocaelisporSüper Lig · Turkey | 3–0 | Süper Lig · Turkey |
| 1999-12-25 | FenerbahcevErzurumsporSüper Lig · Turkey | 2–0 | Süper Lig · Turkey |
| 1999-12-24 | BursasporvBesiktasSüper Lig · Turkey | 0–1 | Süper Lig · Turkey |
| 1999-12-23 | Cataloniav Serbiaplayed as FR YugoslaviaFriendly | 1–0 | Friendly |
| 1999-12-23 |  Libyav GabonFriendly | 2–0 | Friendly |
| 1999-12-22 | ZaragozavLa CorunaLa Liga · Spain | 2–1 | La Liga · Spain |
| 1999-12-22 | VallecanovBarcelonaLa Liga · Spain | 1–1 | La Liga · Spain |
| 1999-12-22 | EspanolvNumanciaLa Liga · Spain | 3–1 | La Liga · Spain |
| 1999-12-22 | CeltavMalagaLa Liga · Spain | 2–4 | La Liga · Spain |
| 1999-12-22 | PaniliakosvIonikosSuper League · Greece | 3–0 | Super League · Greece |
| 1999-12-22 | XanthivPanathinaikosSuper League · Greece | 1–3 | Super League · Greece |
| 1999-12-22 | Ath MadridvOviedoLa Liga · Spain | 5–0 | La Liga · Spain |
| 1999-12-22 | SantandervAth BilbaoLa Liga · Spain | 2–2 | La Liga · Spain |
| 1999-12-22 |  Tunisiav GhanaFriendly | 2–0 | Friendly |
| 1999-12-22 | MallorcavSevillaLa Liga · Spain | 3–1 | La Liga · Spain |
| 1999-12-22 | FenerbahcevGalatasaraySüper Lig · Turkey | 1–2 | Süper Lig · Turkey |
| 1999-12-22 | SociedadvValenciaLa Liga · Spain | 0–0 | La Liga · Spain |
| 1999-12-22 | ApollonvKavalaSuper League · Greece | 0–2 | Super League · Greece |
| 1999-12-22 | PanioniosvTrikalaSuper League · Greece | 4–1 | Super League · Greece |
| 1999-12-22 | OlympiakosvKalamataSuper League · Greece | 4–1 | Super League · Greece |
| 1999-12-22 | RangersvHeartsPremiership · Scotland | 1–0 | Premiership · Scotland |
| 1999-12-22 | ProodeytikivAEKSuper League · Greece | 1–4 | Super League · Greece |
| 1999-12-22 | BetisvValladolidLa Liga · Spain | 0–1 | La Liga · Spain |
| 1999-12-22 | CowdenbeathvQueens ParkLeague Two · Scotland | 0–2 | League Two · Scotland |
| 1999-12-22 | Ethnikos AsterasvOFISuper League · Greece | 0–1 | Super League · Greece |
| 1999-12-21 | AlavesvReal MadridLa Liga · Spain | 1–3 | La Liga · Spain |
| 1999-12-21 |  Moroccov SenegalFriendly | 0–0 | Friendly |
| 1999-12-21 | PanahaikivPAOKSuper League · Greece | 1–2 | Super League · Greece |