| 1999-05-01 | Ross CountyvAlbion RvsLeague Two · Scotland | 2–0 | League Two · Scotland |
| 1999-05-01 | LivingstonvInverness CLeague One · Scotland | 4–3 | League One · Scotland |
| 1999-05-01 | BerwickvMontroseLeague Two · Scotland | 4–1 | League Two · Scotland |
| 1999-05-01 | ClydevStirlingLeague One · Scotland | 4–1 | League One · Scotland |
| 1999-05-01 | HartlepoolvCarlisleLeague Two · England | 0–0 | League Two · England |
| 1999-05-01 | Crystal PalacevHuddersfieldChampionship · England | 2–2 | Championship · England |
| 1999-05-01 | CoventryvWimbledonPremier League · England | 2–1 | Premier League · England |
| 1999-05-01 | Port ValevQPRChampionship · England | 2–0 | Championship · England |
| 1999-05-01 | PeterborovLeyton OrientLeague Two · England | 3–0 | League Two · England |
| 1999-05-01 | CambuurvHeerenveenEredivisie · Netherlands | 0–0 | Eredivisie · Netherlands |
| 1999-05-01 | PrestonvNotts CountyLeague One · England | 1–1 | League One · England |
| 1999-05-01 | FalkirkvClydebankChampionship · Scotland | 0–2 | Championship · Scotland |
| 1999-05-01 | BarnetvSouthendLeague Two · England | 0–2 | League Two · England |
| 1999-05-01 | HalifaxvScarboroughLeague Two · England | 1–2 | League Two · England |
| 1999-05-01 |  Maldivesv NepalSAFF Cup | 2–0 | SAFF Cup |
| 1999-05-01 | MontpelliervNantesLigue 1 · France | 1–2 | Ligue 1 · France |
| 1999-05-01 | LutonvMacclesfieldLeague One · England | 1–2 | League One · England |
| 1999-05-01 | Man UnitedvAston VillaPremier League · England | 2–1 | Premier League · England |
| 1999-05-01 | WalsallvOldhamLeague One · England | 3–1 | League One · England |
| 1999-05-01 | KarabuksporvBesiktasSüper Lig · Turkey | 1–2 | Süper Lig · Turkey |
| 1999-05-01 | CrewevPortsmouthChampionship · England | 3–1 | Championship · England |
| 1999-05-01 | West HamvLeedsPremier League · England | 1–5 | Premier League · England |
| 1999-05-01 | LeverkusenvHerthaBundesliga · Germany | 2–2 | Bundesliga · Germany |
| 1999-05-01 | Raith RvsvSt MirrenChampionship · Scotland | 1–1 | Championship · Scotland |
| 1999-05-01 | HullvTorquayLeague Two · England | 1–0 | League Two · England |
| 1999-05-01 | Hansa RostockvMunich 1860Bundesliga · Germany | 4–1 | Bundesliga · Germany |
| 1999-05-01 | WrexhamvWiganLeague One · England | 0–2 | League One · England |
| 1999-05-01 | LiverpoolvTottenhamPremier League · England | 3–2 | Premier League · England |
| 1999-05-01 | Dundee UnitedvDundeePremiership · Scotland | 0–2 | Premiership · Scotland |
| 1999-05-01 | PartickvForfarLeague One · Scotland | 1–0 | League One · Scotland |
| 1999-05-01 | Bristol RvsvMan CityLeague One · England | 2–2 | League One · England |
| 1999-05-01 | Bayern MunichvM'gladbachBundesliga · Germany | 4–2 | Bundesliga · Germany |
| 1999-05-01 | ValenciavAlavesLa Liga · Spain | 5–0 | La Liga · Spain |
| 1999-05-01 | RennesvParis SGLigue 1 · France | 2–1 | Ligue 1 · France |
| 1999-05-01 | BrentfordvExeterLeague Two · England | 3–0 | League Two · England |
| 1999-05-01 | BarnsleyvWatfordChampionship · England | 2–2 | Championship · England |
| 1999-05-01 | Roda JCvGraafschapEredivisie · Netherlands | 3–1 | Eredivisie · Netherlands |
| 1999-05-01 | BradfordvOxfordChampionship · England | 0–0 | Championship · England |
| 1999-05-01 | BastiavLensLigue 1 · France | 1–1 | Ligue 1 · France |
| 1999-05-01 | BurnleyvFulhamLeague One · England | 1–0 | League One · England |
| 1999-05-01 | Le MansvLavalLigue 2 · France | 0–0 | Ligue 2 · France |
| 1999-05-01 | TwentevFor SittardEredivisie · Netherlands | 2–2 | Eredivisie · Netherlands |
| 1999-05-01 | AlloavEast FifeLeague One · Scotland | 3–1 | League One · Scotland |
| 1999-05-01 | PlymouthvCambridgeLeague Two · England | 2–2 | League Two · England |
| 1999-05-01 | AberdeenvSt JohnstonePremiership · Scotland | 1–0 | Premiership · Scotland |
| 1999-05-01 | BeverenvWesterloPro League · Belgium | 1–0 | Pro League · Belgium |
| 1999-05-01 | WolfsburgvStuttgartBundesliga · Germany | 3–2 | Bundesliga · Germany |
| 1999-05-01 | EleysinavPAOKSuper League · Greece | 0–4 | Super League · Greece |
| 1999-05-01 | LeiriavSp LisbonPrimeira Liga · Portugal | 0–3 | Primeira Liga · Portugal |
| 1999-05-01 | Real MadridvEspanolLa Liga · Spain | 2–0 | La Liga · Spain |