| 1999-02-21 | M'gladbachvKaiserslauternBundesliga · Germany | 0–2 | Bundesliga · Germany |
| 1999-02-21 | CeltavBarcelonaLa Liga · Spain | 0–0 | La Liga · Spain |
| 1999-02-21 | LogronesvBarcelona BLa Liga 2 · Spain | 0–1 | La Liga 2 · Spain |
| 1999-02-21 | PortovAlvercaPrimeira Liga · Portugal | 3–1 | Primeira Liga · Portugal |
| 1999-02-21 | OviedovMallorcaLa Liga · Spain | 1–3 | La Liga · Spain |
| 1999-02-21 | ApollonvPanioniosSuper League · Greece | 0–0 | Super League · Greece |
| 1999-02-21 | AEKvEleysinaSuper League · Greece | 6–2 | Super League · Greece |
| 1999-02-21 | SetubalvMaritimoPrimeira Liga · Portugal | 3–1 | Primeira Liga · Portugal |
| 1999-02-21 | OurensevMeridaLa Liga 2 · Spain | 0–1 | La Liga 2 · Spain |
| 1999-02-21 | CampomaiorensevEst AmadoraPrimeira Liga · Portugal | 3–0 | Primeira Liga · Portugal |
| 1999-02-21 | AnkaragucuvGaziantepsporSüper Lig · Turkey | 1–1 | Süper Lig · Turkey |
| 1999-02-21 | BolognavEmpoliSerie A · Italy | 2–0 | Serie A · Italy |
| 1999-02-21 | WimbledonvAston VillaPremier League · England | 0–0 | Premier League · England |
| 1999-02-21 | ValenciavValladolidLa Liga · Spain | 0–1 | La Liga · Spain |
| 1999-02-21 | PAOKvKavalaSuper League · Greece | 1–0 | Super League · Greece |
| 1999-02-21 | AlavesvTenerifeLa Liga · Spain | 3–1 | La Liga · Spain |
| 1999-02-21 | SalernitanavParmaSerie A · Italy | 1–2 | Serie A · Italy |
| 1999-02-21 | VeneziavPerugiaSerie A · Italy | 2–1 | Serie A · Italy |
| 1999-02-21 | KarabuksporvErzurumSüper Lig · Turkey | 1–1 | Süper Lig · Turkey |
| 1999-02-21 |  United Statesv ChileFriendly | 2–1 | Friendly |
| 1999-02-21 | FiorentinavRomaSerie A · Italy | 0–0 | Serie A · Italy |
| 1999-02-21 | AcademicavBeira MarPrimeira Liga · Portugal | 1–0 | Primeira Liga · Portugal |
| 1999-02-21 | AdanasporvGenclerbirligiSüper Lig · Turkey | 1–1 | Süper Lig · Turkey |
| 1999-02-21 | TernanavAtalantaSerie B · Italy | 1–1 | Serie B · Italy |
| 1999-02-21 | ProodeytikivEthnikos PiraeusSuper League · Greece | 0–0 | Super League · Greece |
| 1999-02-21 | CremonesevBresciaSerie B · Italy | 1–2 | Serie B · Italy |
| 1999-02-21 | SalamancavVillarealLa Liga · Spain | 1–0 | La Liga · Spain |
| 1999-02-21 | SampdoriavPiacenzaSerie A · Italy | 3–2 | Serie A · Italy |
| 1999-02-21 | TrabzonsporvKocaelisporSüper Lig · Turkey | 0–3 | Süper Lig · Turkey |
| 1999-02-21 | XanthivOFISuper League · Greece | 3–1 | Super League · Greece |
| 1999-02-21 | RavennavGenoaSerie B · Italy | 2–1 | Serie B · Italy |
| 1999-02-21 | SociedadvAth MadridLa Liga · Spain | 3–2 | La Liga · Spain |
| 1999-02-21 | NapolivReggianaSerie B · Italy | 2–0 | Serie B · Italy |
| 1999-02-21 | IraklisvPaniliakosSuper League · Greece | 3–1 | Super League · Greece |
| 1999-02-21 | MonzavCesenaSerie B · Italy | 0–1 | Serie B · Italy |
| 1999-02-21 | MotherwellvCelticPremiership · Scotland | 1–7 | Premiership · Scotland |
| 1999-02-21 | LeccevF. AndriaSerie B · Italy | 1–0 | Serie B · Italy |
| 1999-02-20 | LleidavHerculesLa Liga 2 · Spain | 1–0 | La Liga 2 · Spain |
| 1999-02-20 | SouthamptonvNewcastlePremier League · England | 2–1 | Premier League · England |
| 1999-02-20 | StuttgartvSchalke 04Bundesliga · Germany | 2–1 | Bundesliga · Germany |
| 1999-02-20 | AnderlechtvGerminalPro League · Belgium | 2–0 | Pro League · Belgium |
| 1999-02-20 | ReadingvPrestonLeague One · England | 2–1 | League One · England |
| 1999-02-20 | FalkirkvHibernianChampionship · Scotland | 1–2 | Championship · Scotland |
| 1999-02-20 | HullvBarnetLeague Two · England | 1–1 | League Two · England |
| 1999-02-20 | SantandervZaragozaLa Liga · Spain | 2–4 | La Liga · Spain |
| 1999-02-20 | BlackpoolvLincolnLeague One · England | 0–1 | League One · England |
| 1999-02-20 | BarnsleyvGrimsbyChampionship · England | 0–0 | Championship · England |
| 1999-02-20 | Munich 1860vEin FrankfurtBundesliga · Germany | 4–1 | Bundesliga · Germany |
| 1999-02-20 | BesiktasvAltaySüper Lig · Turkey | 1–1 | Süper Lig · Turkey |
| 1999-02-20 | BuryvNorwichChampionship · England | 0–2 | Championship · England |