| 1999-12-28 | QPRvCreweChampionship · England | 1–0 | Championship · England |
| 1999-12-28 | HullvMansfieldLeague Two · England | 2–0 | League Two · England |
| 1999-12-28 | WatfordvSouthamptonPremier League · England | 3–2 | Premier League · England |
| 1999-12-28 | BurnleyvOxfordLeague One · England | 3–2 | League One · England |
| 1999-12-28 | BradfordvEvertonPremier League · England | 0–0 | Premier League · England |
| 1999-12-28 | BarnetvHalifaxLeague Two · England | 0–1 | League Two · England |
| 1999-12-28 | BarnsleyvPort ValeChampionship · England | 3–1 | Championship · England |
| 1999-12-28 | Bristol CityvLutonLeague One · England | 0–0 | League One · England |
| 1999-12-27 | DundeevSt JohnstonePremiership · Scotland | 1–1 | Premiership · Scotland |
| 1999-12-27 | AberdeenvDundee UnitedPremiership · Scotland | 3–1 | Premiership · Scotland |
| 1999-12-27 | StranraervClydeLeague One · Scotland | 2–2 | League One · Scotland |
| 1999-12-27 | AyrvAirdrieChampionship · Scotland | 5–0 | Championship · Scotland |
| 1999-12-27 | CelticvRangersPremiership · Scotland | 1–1 | Premiership · Scotland |
| 1999-12-27 | BerwickvMontroseLeague Two · Scotland | 0–0 | League Two · Scotland |
| 1999-12-27 | FalkirkvLivingstonChampionship · Scotland | 2–3 | Championship · Scotland |
| 1999-12-27 | HamiltonvStirlingLeague One · Scotland | 0–2 | League One · Scotland |
| 1999-12-27 |  Gabonv TogoFriendly | 3–2 | Friendly |
| 1999-12-27 | HibernianvKilmarnockPremiership · Scotland | 2–2 | Premiership · Scotland |
| 1999-12-27 | ArbroathvPartickLeague One · Scotland | 0–0 | League One · Scotland |
| 1999-12-27 | Inverness CvClydebankChampionship · Scotland | 4–1 | Championship · Scotland |
| 1999-12-27 | MortonvRaith RvsChampionship · Scotland | 1–0 | Championship · Scotland |
| 1999-12-26 | MansfieldvChesterLeague Two · England | 2–1 | League Two · England |
| 1999-12-26 | HartlepoolvYorkLeague Two · England | 2–1 | League Two · England |
| 1999-12-26 | BirminghamvSheffield UnitedChampionship · England | 0–2 | Championship · England |
| 1999-12-26 | Man UnitedvBradfordPremier League · England | 4–0 | Premier League · England |
| 1999-12-26 | Bristol RvsvMillwallLeague One · England | 1–0 | League One · England |
| 1999-12-26 | BlackpoolvStokeLeague One · England | 1–2 | League One · England |
| 1999-12-26 | BrentfordvBristol CityLeague One · England | 2–1 | League One · England |
| 1999-12-26 | ShrewsburyvMacclesfieldLeague Two · England | 0–1 | League Two · England |
| 1999-12-26 | OxfordvCambridgeLeague One · England | 1–0 | League One · England |
| 1999-12-26 | Notts CountyvWiganLeague One · England | 0–2 | League One · England |
| 1999-12-26 | CrewevHuddersfieldChampionship · England | 1–1 | Championship · England |
| 1999-12-26 | SwindonvPortsmouthChampionship · England | 1–1 | Championship · England |
| 1999-12-26 | TottenhamvWatfordPremier League · England | 4–0 | Premier League · England |
| 1999-12-26 | BrightonvBarnetLeague Two · England | 1–1 | League Two · England |
| 1999-12-26 | OldhamvScunthorpeLeague One · England | 1–1 | League One · England |
| 1999-12-26 | HalifaxvLincolnLeague Two · England | 3–0 | League Two · England |
| 1999-12-26 | PeterborovRotherhamLeague Two · England | 0–5 | League Two · England |
| 1999-12-26 | DarlingtonvHullLeague Two · England | 0–0 | League Two · England |
| 1999-12-26 | Sheffield WedsvMiddlesbroughPremier League · England | 1–0 | Premier League · England |
| 1999-12-26 | LeedsvLeicesterPremier League · England | 2–1 | Premier League · England |
| 1999-12-26 | TrabzonsporvIstanbulsporSüper Lig · Turkey | 1–1 | Süper Lig · Turkey |
| 1999-12-26 | GalatasarayvVansporSüper Lig · Turkey | 2–1 | Süper Lig · Turkey |
| 1999-12-26 | SouthamptonvChelseaPremier League · England | 1–2 | Premier League · England |
| 1999-12-26 | CheltenhamvExeterLeague Two · England | 3–1 | League Two · England |
| 1999-12-26 | StockportvWolvesChampionship · England | 3–2 | Championship · England |
| 1999-12-26 | CardiffvReadingLeague One · England | 1–0 | League One · England |
| 1999-12-26 | EvertonvSunderlandPremier League · England | 5–0 | Premier League · England |
| 1999-12-26 | BuryvBurnleyLeague One · England | 4–2 | League One · England |
| 1999-12-26 | Leyton OrientvSwanseaLeague Two · England | 0–1 | League Two · England |