| 1999-05-02 | MonzavLecceSerie B · Italy | 1–1 | Serie B · Italy |
| 1999-05-02 | CesenavVeronaSerie B · Italy | 2–0 | Serie B · Italy |
| 1999-05-02 | ArsenalvDerbyPremier League · England | 1–0 | Premier League · England |
| 1999-05-02 | OurensevLas PalmasLa Liga 2 · Spain | 4–1 | La Liga 2 · Spain |
| 1999-05-02 | AlvercavRio AvePrimeira Liga · Portugal | 0–1 | Primeira Liga · Portugal |
| 1999-05-02 | ParmavEmpoliSerie A · Italy | 1–0 | Serie A · Italy |
| 1999-05-02 | BarcelonavLa CorunaLa Liga · Spain | 4–0 | La Liga · Spain |
| 1999-05-02 | ArisvAEKSuper League · Greece | 2–0 | Super League · Greece |
| 1999-05-01 | BeauvaisvNiortLigue 2 · France | 3–2 | Ligue 2 · France |
| 1999-05-01 | StockportvSunderlandChampionship · England | 0–1 | Championship · England |
| 1999-05-01 | HamburgvKaiserslauternBundesliga · Germany | 2–0 | Bundesliga · Germany |
| 1999-05-01 | RotherhamvBrightonLeague Two · England | 2–1 | League Two · England |
| 1999-05-01 | LillevAmiensLigue 2 · France | 0–1 | Ligue 2 · France |
| 1999-05-01 | CardiffvScunthorpeLeague Two · England | 0–0 | League Two · England |
| 1999-05-01 | SouthamptonvLeicesterPremier League · England | 2–1 | Premier League · England |
| 1999-05-01 |  Indiav BangladeshSAFF Cup | 2–0 | SAFF Cup |
| 1999-05-01 | Sheffield UnitedvBristol CityChampionship · England | 3–1 | Championship · England |
| 1999-05-01 | GentvLommelPro League · Belgium | 2–2 | Pro League · Belgium |
| 1999-05-01 | TroyesvCaenLigue 2 · France | 0–1 | Ligue 2 · France |
| 1999-05-01 | NimesvGuingampLigue 2 · France | 0–0 | Ligue 2 · France |
| 1999-05-01 | NewcastlevMiddlesbroughPremier League · England | 1–1 | Premier League · England |
| 1999-05-01 | ColchestervLincolnLeague One · England | 1–3 | League One · England |
| 1999-05-01 | GuimaraesvBeira MarPrimeira Liga · Portugal | 3–0 | Primeira Liga · Portugal |
| 1999-05-01 | GillinghamvStokeLeague One · England | 4–0 | League One · England |
| 1999-05-01 | GrimsbyvTranmereChampionship · England | 1–0 | Championship · England |
| 1999-05-01 | CowdenbeathvStenhousemuirLeague Two · Scotland | 0–2 | League Two · Scotland |
| 1999-05-01 | NicevValenceLigue 2 · France | 2–0 | Ligue 2 · France |
| 1999-05-01 | ChelseavEvertonPremier League · England | 3–1 | Premier League · England |
| 1999-05-01 | MortonvAyrChampionship · Scotland | 1–4 | Championship · Scotland |
| 1999-05-01 | PSV EindhovenvWaalwijkEredivisie · Netherlands | 2–2 | Eredivisie · Netherlands |
| 1999-05-01 | StranraervHibernianChampionship · Scotland | 0–4 | Championship · Scotland |
| 1999-05-01 | MetzvAuxerreLigue 1 · France | 2–0 | Ligue 1 · France |
| 1999-05-01 | CharltonvBlackburnPremier League · England | 0–0 | Premier League · England |
| 1999-05-01 | WycombevBlackpoolLeague One · England | 2–2 | League One · England |
| 1999-05-01 | YorkvBournemouthLeague One · England | 0–1 | League One · England |
| 1999-05-01 | KilmarnockvMotherwellPremiership · Scotland | 0–1 | Premiership · Scotland |
| 1999-05-01 | Nott'm ForestvSheffield WedsPremier League · England | 2–0 | Premier League · England |
| 1999-05-01 | NorwichvSwindonChampionship · England | 2–1 | Championship · England |
| 1999-05-01 | StrasbourgvSochauxLigue 1 · France | 1–1 | Ligue 1 · France |
| 1999-05-01 | DarlingtonvChesterLeague Two · England | 1–2 | League Two · England |
| 1999-05-01 | West BromvBuryChampionship · England | 1–0 | Championship · England |
| 1999-05-01 | LiersevLokerenPro League · Belgium | 2–3 | Pro League · Belgium |
| 1999-05-01 | ArbroathvQueen of SthLeague One · Scotland | 0–2 | League One · Scotland |
| 1999-05-01 | OostendevHarelbekePro League · Belgium | 1–0 | Pro League · Belgium |
| 1999-05-01 | Le HavrevNancyLigue 1 · France | 1–1 | Ligue 1 · France |
| 1999-05-01 | GueugnonvChateaurouxLigue 2 · France | 2–1 | Ligue 2 · France |
| 1999-05-01 | DumbartonvQueens ParkLeague Two · Scotland | 0–1 | League Two · Scotland |
| 1999-05-01 | AirdrievHamiltonChampionship · Scotland | 1–0 | Championship · Scotland |
| 1999-05-01 | BrechinvEast StirlingLeague Two · Scotland | 1–0 | League Two · Scotland |
| 1999-05-01 | St EtiennevAjaccioLigue 2 · France | 2–2 | Ligue 2 · France |