| 1999-02-06 | PortsmouthvTranmereChampionship · England | 1–1 | Championship · England |
| 1999-02-06 | NantesvLensLigue 1 · France | 2–0 | Ligue 1 · France |
| 1999-02-06 | TorquayvScunthorpeLeague Two · England | 1–0 | League Two · England |
| 1999-02-06 | ChateaurouxvCaenLigue 2 · France | 2–1 | Ligue 2 · France |
| 1999-02-06 | GenclerbirligivFenerbahceSüper Lig · Turkey | 0–3 | Süper Lig · Turkey |
| 1999-02-06 | St EtiennevLe MansLigue 2 · France | 1–0 | Ligue 2 · France |
| 1999-02-06 | TwentevAZ AlkmaarEredivisie · Netherlands | 0–3 | Eredivisie · Netherlands |
| 1999-02-05 |  British Virgin Islandsv MontserratCFU Caribbean Cup qualification | 3–1 | CFU Caribbean Cup qualification |
| 1999-02-05 | Bristol CityvQPRChampionship · England | 0–0 | Championship · England |
| 1999-02-05 | SwanseavBrightonLeague Two · England | 2–2 | League Two · England |
| 1999-02-05 | ColchestervYorkLeague One · England | 2–1 | League One · England |
| 1999-02-05 |  Greecev BelgiumCyprus International Tournament | 1–0 | Cyprus International Tournament |
| 1999-02-05 | PortovMaritimoPrimeira Liga · Portugal | 1–0 | Primeira Liga · Portugal |
| 1999-02-05 |  Cyprusv FinlandCyprus International Tournament | 2–1 | Cyprus International Tournament |
| 1999-02-05 | BenficavFarensePrimeira Liga · Portugal | 5–0 | Primeira Liga · Portugal |
| 1999-02-05 | NijmegenvGraafschapEredivisie · Netherlands | 1–1 | Eredivisie · Netherlands |
| 1999-02-05 | BesiktasvAntalyasporSüper Lig · Turkey | 2–1 | Süper Lig · Turkey |
| 1999-02-03 | GreecevFinlandCyprus International Tournament | 2–1 | Cyprus International Tournament |
| 1999-02-03 |  Martiniquev French GuianaCFU Caribbean Cup qualification | 3–1 | CFU Caribbean Cup qualification |
| 1999-02-03 |  Maltav PolandFriendly | 0–1 | Friendly |
| 1999-02-03 |  Venezuelav ArgentinaFriendly | 0–2 | Friendly |
| 1999-02-03 | CyprusvBelgiumCyprus International Tournament | 0–1 | Cyprus International Tournament |
| 1999-02-02 | BrentfordvCarlisleLeague Two · England | 1–1 | League Two · England |
| 1999-02-02 | ForfarvClydeLeague One · Scotland | 3–1 | League One · Scotland |
| 1999-02-02 | DumbartonvBerwickLeague Two · Scotland | 1–1 | League Two · Scotland |
| 1999-02-02 | Man UnitedvDerbyPremier League · England | 1–0 | Premier League · England |
| 1999-02-01 | GuimaraesvSalgueirosPrimeira Liga · Portugal | 3–3 | Primeira Liga · Portugal |
| 1999-01-31 | BarcelonavSantanderLa Liga · Spain | 3–2 | La Liga · Spain |
| 1999-01-31 | GerminalvLommelPro League · Belgium | 1–0 | Pro League · Belgium |
| 1999-01-31 | CagliarivJuventusSerie A · Italy | 1–0 | Serie A · Italy |
| 1999-01-31 | IonikosvEthnikos AsterasSuper League · Greece | 5–0 | Super League · Greece |
| 1999-01-31 | MaritimovSp BragaPrimeira Liga · Portugal | 3–0 | Primeira Liga · Portugal |
| 1999-01-31 | EleysinavIraklisSuper League · Greece | 0–0 | Super League · Greece |
| 1999-01-31 | OurensevSevillaLa Liga 2 · Spain | 2–3 | La Liga 2 · Spain |
| 1999-01-31 | GaziantepsporvTrabzonsporSüper Lig · Turkey | 1–1 | Süper Lig · Turkey |
| 1999-01-31 | IstanbulsporvAdanasporSüper Lig · Turkey | 6–0 | Süper Lig · Turkey |
| 1999-01-31 | PescaravVeronaSerie B · Italy | 1–1 | Serie B · Italy |
| 1999-01-31 | F. AndriavRavennaSerie B · Italy | 3–2 | Serie B · Italy |
| 1999-01-31 | ReggianavTernanaSerie B · Italy | 1–1 | Serie B · Italy |
| 1999-01-31 | TenerifevEspanolLa Liga · Spain | 0–0 | La Liga · Spain |
| 1999-01-31 | ValladolidvExtremaduraLa Liga · Spain | 0–0 | La Liga · Spain |
| 1999-01-31 | TorinovCremoneseSerie B · Italy | 5–3 | Serie B · Italy |
| 1999-01-31 | PanathinaikosvOFISuper League · Greece | 1–0 | Super League · Greece |
| 1999-01-31 | KortrijkvStandardPro League · Belgium | 1–3 | Pro League · Belgium |
| 1999-01-31 |  Ethiopiav KenyaFriendly | 2–2 | Friendly |
| 1999-01-31 | KavalavPaniliakosSuper League · Greece | 1–1 | Super League · Greece |
| 1999-01-31 | AntalyasporvSakaryasporSüper Lig · Turkey | 2–2 | Süper Lig · Turkey |
| 1999-01-31 | ParmavVeneziaSerie A · Italy | 2–2 | Serie A · Italy |
| 1999-01-31 | ApollonvXanthiSuper League · Greece | 2–1 | Super League · Greece |
| 1999-01-31 | Sp LisbonvAcademicaPrimeira Liga · Portugal | 5–0 | Primeira Liga · Portugal |