| 1999-02-27 | Hansa RostockvBayern MunichBundesliga · Germany | 0–4 | Bundesliga · Germany |
| 1999-02-27 | PSV EindhovenvNAC BredaEredivisie · Netherlands | 2–0 | Eredivisie · Netherlands |
| 1999-02-27 | NicevTroyesLigue 2 · France | 0–0 | Ligue 2 · France |
| 1999-02-27 | NorthamptonvMillwallLeague One · England | 1–2 | League One · England |
| 1999-02-27 | OFIvOlympiakosSuper League · Greece | 1–2 | Super League · Greece |
| 1999-02-27 | BurnleyvGillinghamLeague One · England | 0–5 | League One · England |
| 1999-02-27 | LommelvAalstPro League · Belgium | 0–3 | Pro League · Belgium |
| 1999-02-27 | ChesterfieldvMan CityLeague One · England | 1–1 | League One · England |
| 1999-02-27 | Aston VillavCoventryPremier League · England | 1–4 | Premier League · England |
| 1999-02-27 | Ath BilbaovCeltaLa Liga · Spain | 0–0 | La Liga · Spain |
| 1999-02-27 | TranmerevBuryChampionship · England | 4–0 | Championship · England |
| 1999-02-27 | Man UnitedvSouthamptonPremier League · England | 2–1 | Premier League · England |
| 1999-02-27 | CharleroivGentPro League · Belgium | 1–1 | Pro League · Belgium |
| 1999-02-27 | ForfarvPartickLeague One · Scotland | 2–1 | League One · Scotland |
| 1999-02-27 | StockportvQPRChampionship · England | 0–0 | Championship · England |
| 1999-02-27 | Albion RvsvRoss CountyLeague Two · Scotland | 3–3 | League Two · Scotland |
| 1999-02-27 | HeartsvAberdeenPremiership · Scotland | 0–2 | Premiership · Scotland |
| 1999-02-27 | MacclesfieldvWiganLeague One · England | 0–1 | League One · England |
| 1999-02-27 | BournemouthvWycombeLeague One · England | 2–0 | League One · England |
| 1999-02-27 | St TruidenvAnderlechtPro League · Belgium | 1–4 | Pro League · Belgium |
| 1999-02-27 | SedanvWasquehalLigue 2 · France | 2–0 | Ligue 2 · France |
| 1999-02-27 | CelticvDundee UnitedPremiership · Scotland | 2–1 | Premiership · Scotland |
| 1999-02-27 | ParmavPerugiaSerie A · Italy | 3–1 | Serie A · Italy |
| 1999-02-27 | East StirlingvBrechinLeague Two · Scotland | 4–1 | League Two · Scotland |
| 1999-02-27 |  South Africav GabonAfrican Cup of Nations qualification | 4–1 | African Cup of Nations qualification |
| 1999-02-27 | PrestonvOldhamLeague One · England | 2–1 | League One · England |
| 1999-02-27 | Queens ParkvDumbartonLeague Two · Scotland | 1–1 | League Two · Scotland |
| 1999-02-27 | MouscronvOostendePro League · Belgium | 2–1 | Pro League · Belgium |
| 1999-02-27 | MontrosevBerwickLeague Two · Scotland | 0–3 | League Two · Scotland |
| 1999-02-27 | Willem IIvUtrechtEredivisie · Netherlands | 1–0 | Eredivisie · Netherlands |
| 1999-02-27 | PortsmouthvPort ValeChampionship · England | 4–0 | Championship · England |
| 1999-02-27 | ChelseavLiverpoolPremier League · England | 2–1 | Premier League · England |
| 1999-02-27 | HamburgvLeverkusenBundesliga · Germany | 0–0 | Bundesliga · Germany |
| 1999-02-27 | Rio AvevEst AmadoraPrimeira Liga · Portugal | 1–1 | Primeira Liga · Portugal |
| 1999-02-27 | ToledovVallecanoLa Liga 2 · Spain | 0–1 | La Liga 2 · Spain |
| 1999-02-27 | WolvesvHuddersfieldChampionship · England | 2–2 | Championship · England |
| 1999-02-27 | WesterlovLiersePro League · Belgium | 0–2 | Pro League · Belgium |
| 1999-02-27 | Raith RvsvAirdrieChampionship · Scotland | 0–1 | Championship · Scotland |
| 1999-02-27 | BarnetvExeterLeague Two · England | 0–1 | League Two · England |
| 1999-02-26 | KarlsruhevMainz2. Bundesliga · Germany | 0–1 | 2. Bundesliga · Germany |
| 1999-02-26 | Club BruggevLokerenPro League · Belgium | 4–0 | Pro League · Belgium |
| 1999-02-26 | BastiavToulouseLigue 1 · France | 1–1 | Ligue 1 · France |
| 1999-02-26 |  United States Virgin Islandsv Turks and Caicos IslandsCFU Caribbean Cup qualification | 2–2 | CFU Caribbean Cup qualification |
| 1999-02-26 | WatfordvSwindonChampionship · England | 0–1 | Championship · England |
| 1999-02-26 | MetzvSochauxLigue 1 · France | 1–1 | Ligue 1 · France |
| 1999-02-26 | RennesvNancyLigue 1 · France | 2–1 | Ligue 1 · France |
| 1999-02-26 | KocaelisporvSakaryasporSüper Lig · Turkey | 0–1 | Süper Lig · Turkey |
| 1999-02-26 | Werder BremenvBochumBundesliga · Germany | 1–1 | Bundesliga · Germany |
| 1999-02-26 | Le HavrevLorientLigue 1 · France | 0–1 | Ligue 1 · France |
| 1999-02-26 | LeiriavSp BragaPrimeira Liga · Portugal | 0–0 | Primeira Liga · Portugal |