| 1999-02-20 | CarlislevMansfieldLeague Two · England | 0–0 | League Two · England |
| 1999-02-20 | OldhamvNorthamptonLeague One · England | 0–1 | League One · England |
| 1999-02-20 | DerbyvCharltonPremier League · England | 0–2 | Premier League · England |
| 1999-02-20 | SunderlandvWolvesChampionship · England | 2–1 | Championship · England |
| 1999-02-20 | HuddersfieldvTranmereChampionship · England | 0–0 | Championship · England |
| 1999-02-20 | PartickvQueen of SthLeague One · Scotland | 1–3 | League One · Scotland |
| 1999-02-20 | RotherhamvBrentfordLeague Two · England | 2–4 | League Two · England |
| 1999-02-20 | AZ AlkmaarvWaalwijkEredivisie · Netherlands | 2–1 | Eredivisie · Netherlands |
| 1999-02-20 | HerthavDortmundBundesliga · Germany | 3–0 | Bundesliga · Germany |
| 1999-02-20 | SwindonvPortsmouthChampionship · England | 3–3 | Championship · England |
| 1999-02-20 | WycombevBurnleyLeague One · England | 2–0 | League One · England |
| 1999-02-20 | VallecanovAlbaceteLa Liga 2 · Spain | 2–0 | La Liga 2 · Spain |
| 1999-02-20 | CrewevStockportChampionship · England | 0–2 | Championship · England |
| 1999-02-20 | HeartsvSt JohnstonePremiership · Scotland | 0–2 | Premiership · Scotland |
| 1999-02-20 | WiganvBournemouthLeague One · England | 2–1 | League One · England |
| 1999-02-20 | MillwallvStokeLeague One · England | 2–0 | League One · England |
| 1999-02-20 | Roda JCvSpartaEredivisie · Netherlands | 1–0 | Eredivisie · Netherlands |
| 1999-02-20 | LivingstonvForfarLeague One · Scotland | 3–0 | League One · Scotland |
| 1999-02-20 | CowdenbeathvMontroseLeague Two · Scotland | 1–0 | League Two · Scotland |
| 1999-02-20 | TorquayvChesterLeague Two · England | 0–3 | League Two · England |
| 1999-02-20 |  Zimbabwev ZambiaFriendly | 1–1 | Friendly |
| 1999-02-20 | IonikosvArisSuper League · Greece | 3–0 | Super League · Greece |
| 1999-02-20 |  Botswanav South AfricaCOSAFA Cup qualification | 1–2 | COSAFA Cup qualification |
| 1999-02-20 | RangersvDundeePremiership · Scotland | 6–1 | Premiership · Scotland |
| 1999-02-20 | SalgueirosvLeiriaPrimeira Liga · Portugal | 0–0 | Primeira Liga · Portugal |
| 1999-02-20 | Sp BragavBoavistaPrimeira Liga · Portugal | 1–2 | Primeira Liga · Portugal |
| 1999-02-20 | MiddlesbroughvTottenhamPremier League · England | 0–0 | Premier League · England |
| 1999-02-20 | QPRvWatfordChampionship · England | 1–2 | Championship · England |
| 1999-02-20 | VitessevMVV MaastrichtEredivisie · Netherlands | 2–1 | Eredivisie · Netherlands |
| 1999-02-20 | Nott'm ForestvChelseaPremier League · England | 1–3 | Premier League · England |
| 1999-02-20 | DuisburgvBayern MunichBundesliga · Germany | 0–3 | Bundesliga · Germany |
| 1999-02-20 | GillinghamvColchesterLeague One · England | 1–1 | League One · England |
| 1999-02-20 | Mallorca BvEibarLa Liga 2 · Spain | 0–1 | La Liga 2 · Spain |
| 1999-02-20 | MalagavRecreativoLa Liga 2 · Spain | 3–1 | La Liga 2 · Spain |
| 1999-02-20 | MortonvHamiltonChampionship · Scotland | 3–0 | Championship · Scotland |
| 1999-02-20 | Man CityvMacclesfieldLeague One · England | 2–0 | League One · England |
| 1999-02-20 | LeedsvEvertonPremier League · England | 1–0 | Premier League · England |
| 1999-02-20 | NurnbergvWerder BremenBundesliga · Germany | 1–1 | Bundesliga · Germany |
| 1999-02-20 | BrechinvStenhousemuirLeague Two · Scotland | 0–2 | League Two · Scotland |
| 1999-02-20 | FulhamvNotts CountyLeague One · England | 2–1 | League One · England |
| 1999-02-20 | LeverkusenvFreiburgBundesliga · Germany | 1–1 | Bundesliga · Germany |
| 1999-02-20 | Real MadridvAth BilbaoLa Liga · Spain | 0–1 | La Liga · Spain |
| 1999-02-20 | Port ValevCrystal PalaceChampionship · England | 1–0 | Championship · England |
| 1999-02-20 | Las PalmasvSp GijonLa Liga 2 · Spain | 3–0 | La Liga 2 · Spain |
| 1999-02-20 | ClydevEast FifeLeague One · Scotland | 1–0 | League One · Scotland |
| 1999-02-20 | Bristol RvsvLutonLeague One · England | 1–0 | League One · England |
| 1999-02-20 | WalsallvChesterfieldLeague One · England | 1–1 | League One · England |
| 1999-02-20 | LiverpoolvWest HamPremier League · England | 2–2 | Premier League · England |
| 1999-02-20 | SouthendvBrightonLeague Two · England | 3–0 | League Two · England |
| 1999-02-20 | ArsenalvLeicesterPremier League · England | 5–0 | Premier League · England |