| 1999-12-30 | ArisvPaniliakosSuper League · Greece | 2–1 | Super League · Greece |
| 1999-12-29 | OFIvIraklisSuper League · Greece | 1–1 | Super League · Greece |
| 1999-12-29 |  Libyav TogoFriendly | 2–0 | Friendly |
| 1999-12-29 | PanathinaikosvPanahaikiSuper League · Greece | 7–1 | Super League · Greece |
| 1999-12-29 |  Ivory Coastv Burkina FasoFriendly | 3–1 | Friendly |
| 1999-12-29 | ChelseavSheffield WedsPremier League · England | 3–0 | Premier League · England |
| 1999-12-29 | PAOKvProodeytikiSuper League · Greece | 1–0 | Super League · Greece |
| 1999-12-29 | TrikalavApollonSuper League · Greece | 1–0 | Super League · Greece |
| 1999-12-29 | AEKvPanioniosSuper League · Greece | 0–1 | Super League · Greece |
| 1999-12-29 |  Costa Ricav HondurasFriendly | 1–1 | Friendly |
| 1999-12-29 | Aston VillavTottenhamPremier League · England | 1–1 | Premier League · England |
| 1999-12-29 | IonikosvOlympiakosSuper League · Greece | 1–2 | Super League · Greece |
| 1999-12-29 | Basque Countryv NigeriaFriendly | 5–1 | Friendly |
| 1999-12-29 | XanthivEthnikos AsterasSuper League · Greece | 0–0 | Super League · Greece |
| 1999-12-28 | HuddersfieldvCharltonChampionship · England | 1–2 | Championship · England |
| 1999-12-28 | SwanseavPlymouthLeague Two · England | 1–0 | League Two · England |
| 1999-12-28 | ChestervLeyton OrientLeague Two · England | 1–5 | League Two · England |
| 1999-12-28 | ReadingvNotts CountyLeague One · England | 0–0 | League One · England |
| 1999-12-28 |  Malaysiav SingaporeFriendly | 1–0 | Friendly |
| 1999-12-28 | LiverpoolvWimbledonPremier League · England | 3–1 | Premier League · England |
| 1999-12-28 | ExetervPeterboroLeague Two · England | 2–2 | League Two · England |
| 1999-12-28 | PortsmouthvBlackburnChampionship · England | 1–2 | Championship · England |
| 1999-12-28 | KalamatavKavalaSuper League · Greece | 3–2 | Super League · Greece |
| 1999-12-28 | RochdalevShrewsburyLeague Two · England | 2–1 | League Two · England |
| 1999-12-28 | BoltonvWest BromChampionship · England | 1–1 | Championship · England |
| 1999-12-28 | TranmerevSwindonChampionship · England | 3–1 | Championship · England |
| 1999-12-28 | CambridgevCardiffLeague One · England | 0–0 | League One · England |
| 1999-12-28 | Nott'm ForestvBirminghamChampionship · England | 1–0 | Championship · England |
| 1999-12-28 | Andalusiav EstoniaFriendly | 1–0 | Friendly |
| 1999-12-28 | TorquayvSouthendLeague Two · England | 0–1 | League Two · England |
| 1999-12-28 | ScunthorpevBlackpoolLeague One · England | 1–0 | League One · England |
| 1999-12-28 | Sheffield UnitedvFulhamChampionship · England | 2–0 | Championship · England |
| 1999-12-28 | WiganvGillinghamLeague One · England | 2–0 | League One · England |
| 1999-12-28 | PrestonvBristol RvsLeague One · England | 2–1 | League One · England |
| 1999-12-28 | BournemouthvWrexhamLeague One · England | 1–0 | League One · England |
| 1999-12-28 | MillwallvBrentfordLeague One · England | 3–2 | League One · England |
| 1999-12-28 | LeicestervNewcastlePremier League · England | 1–2 | Premier League · England |
| 1999-12-28 | Man CityvGrimsbyChampionship · England | 2–1 | Championship · England |
| 1999-12-28 | NorthamptonvDarlingtonLeague Two · England | 0–3 | League Two · England |
| 1999-12-28 | IpswichvStockportChampionship · England | 1–0 | Championship · England |
| 1999-12-28 | WolvesvNorwichChampionship · England | 1–0 | Championship · England |
| 1999-12-28 | StokevOldhamLeague One · England | 0–0 | League One · England |
| 1999-12-28 | SunderlandvMan UnitedPremier League · England | 2–2 | Premier League · England |
| 1999-12-28 | ArsenalvLeedsPremier League · England | 2–0 | Premier League · England |
| 1999-12-28 | RotherhamvBrightonLeague Two · England | 1–3 | League Two · England |
| 1999-12-28 | LincolnvHartlepoolLeague Two · England | 1–2 | League Two · England |
| 1999-12-28 | West HamvDerbyPremier League · England | 1–1 | Premier League · England |
| 1999-12-28 | YorkvCheltenhamLeague Two · England | 1–2 | League Two · England |
| 1999-12-28 | MacclesfieldvCarlisleLeague Two · England | 2–1 | League Two · England |
| 1999-12-28 | Crystal PalacevWalsallChampionship · England | 3–2 | Championship · England |