| 1999-02-20 | CoventryvMan UnitedPremier League · England | 0–1 | Premier League · England |
| 1999-02-20 | BlackburnvSheffield WedsPremier League · England | 1–4 | Premier League · England |
| 1999-02-20 | CompostelavBadajozLa Liga 2 · Spain | 1–0 | La Liga 2 · Spain |
| 1999-02-20 | ExetervHartlepoolLeague Two · England | 2–1 | League Two · England |
| 1999-02-20 | BerwickvQueens ParkLeague Two · Scotland | 0–2 | League Two · Scotland |
| 1999-02-20 | StranraervClydebankChampionship · Scotland | 0–2 | Championship · Scotland |
| 1999-02-20 | VeronavTrevisoSerie B · Italy | 1–1 | Serie B · Italy |
| 1999-02-20 | For SittardvCambuurEredivisie · Netherlands | 2–0 | Eredivisie · Netherlands |
| 1999-02-20 | Leyton OrientvCambridgeLeague Two · England | 2–0 | League Two · England |
| 1999-02-20 | AlloavInverness CLeague One · Scotland | 1–4 | League One · Scotland |
| 1999-02-20 | ExtremaduravBetisLa Liga · Spain | 2–1 | La Liga · Spain |
| 1999-02-20 | West BromvBristol CityChampionship · England | 2–2 | Championship · England |
| 1999-02-20 | NumanciavOsasunaLa Liga 2 · Spain | 3–0 | La Liga 2 · Spain |
| 1999-02-20 | IpswichvOxfordChampionship · England | 2–1 | Championship · England |
| 1999-02-20 | ArbroathvStirlingLeague One · Scotland | 1–0 | League One · Scotland |
| 1999-02-20 | DarlingtonvPlymouthLeague Two · England | 1–2 | League Two · England |
| 1999-02-20 | Dundee UnitedvAberdeenPremiership · Scotland | 3–0 | Premiership · Scotland |
| 1999-02-20 | PeterborovShrewsburyLeague Two · England | 2–2 | League Two · England |
| 1999-02-20 | Raith RvsvAyrChampionship · Scotland | 2–4 | Championship · Scotland |
| 1999-02-20 | ScunthorpevRochdaleLeague Two · England | 0–1 | League Two · England |
| 1999-02-20 | WrexhamvYorkLeague One · England | 1–1 | League One · England |
| 1999-02-20 |  Gabonv Burkina FasoFriendly | 1–1 | Friendly |
| 1999-02-20 | ScarboroughvSwanseaLeague Two · England | 2–1 | League Two · England |
| 1999-02-19 | Sheffield UnitedvBradfordChampionship · England | 2–2 | Championship · England |
| 1999-02-19 | WolfsburgvHansa RostockBundesliga · Germany | 1–1 | Bundesliga · Germany |
| 1999-02-19 | CardiffvHalifaxLeague Two · England | 1–1 | League Two · England |
| 1999-02-19 | Sp LisbonvRio AvePrimeira Liga · Portugal | 2–0 | Primeira Liga · Portugal |
| 1999-02-19 |  Egyptv MexicoLunar New Year Cup | 0–3 | Lunar New Year Cup |
| 1999-02-19 | SamsunsporvFenerbahceSüper Lig · Turkey | 1–1 | Süper Lig · Turkey |
| 1999-02-18 | PSV EindhovenvTwenteEredivisie · Netherlands | 3–0 | Eredivisie · Netherlands |
| 1999-02-17 | HeerenveenvAjaxEredivisie · Netherlands | 2–2 | Eredivisie · Netherlands |
| 1999-02-17 | EvertonvMiddlesbroughPremier League · England | 5–0 | Premier League · England |
| 1999-02-17 | NewcastlevCoventryPremier League · England | 4–1 | Premier League · England |
| 1999-02-17 | NijmegenvWillem IIEredivisie · Netherlands | 0–3 | Eredivisie · Netherlands |
| 1999-02-17 | WaalwijkvFor SittardEredivisie · Netherlands | 0–0 | Eredivisie · Netherlands |
| 1999-02-17 | Aston VillavLeedsPremier League · England | 1–2 | Premier League · England |
| 1999-02-17 | Man UnitedvArsenalPremier League · England | 1–1 | Premier League · England |
| 1999-02-17 | ChelseavBlackburnPremier League · England | 1–1 | Premier League · England |
| 1999-02-17 | CelticvKilmarnockPremiership · Scotland | 1–0 | Premiership · Scotland |
| 1999-02-17 |  Guatemalav ChileFriendly | 1–1 | Friendly |
| 1999-02-17 | VitessevNAC BredaEredivisie · Netherlands | 3–1 | Eredivisie · Netherlands |
| 1999-02-17 |  Ecuadorv PeruFriendly | 1–2 | Friendly |
| 1999-02-17 | PartickvStirlingLeague One · Scotland | 0–1 | League One · Scotland |
| 1999-02-16 | NorwichvBarnsleyChampionship · England | 0–0 | Championship · England |
| 1999-02-16 | SwanseavBrentfordLeague Two · England | 2–1 | League Two · England |
| 1999-02-16 | LivingstonvArbroathLeague One · Scotland | 1–0 | League One · Scotland |
| 1999-02-16 |  BulgariavEgyptLunar New Year Cup | 1–3 | Lunar New Year Cup |
| 1999-02-16 | East StirlingvAlbion RvsLeague Two · Scotland | 4–1 | League Two · Scotland |
| 1999-02-16 | BrechinvMontroseLeague Two · Scotland | 2–3 | League Two · Scotland |
| 1999-02-16 | DarlingtonvHullLeague Two · England | 0–1 | League Two · England |