| 1999-01-20 |  Israelv NorwayFriendly | 0–1 | Friendly |
| 1999-01-20 | LivingstonvEast FifeLeague One · Scotland | 1–0 | League One · Scotland |
| 1999-01-20 |  Francev MoroccoFriendly | 1–0 | Friendly |
| 1999-01-20 | VeneziavEmpoliSerie A · Italy | 3–2 | Serie A · Italy |
| 1999-01-19 | ArbroathvForfarLeague One · Scotland | 2–2 | League One · Scotland |
| 1999-01-19 | BradfordvCrystal PalaceChampionship · England | 2–1 | Championship · England |
| 1999-01-19 | AirdrievMortonChampionship · Scotland | 0–2 | Championship · Scotland |
| 1999-01-18 | Rio AvevPortoPrimeira Liga · Portugal | 1–1 | Primeira Liga · Portugal |
| 1999-01-18 | Aston VillavEvertonPremier League · England | 3–0 | Premier League · England |
| 1999-01-18 | Israelv EstoniaFriendly | 7–0 | Friendly |
| 1999-01-18 | EleysinavPanathinaikosSuper League · Greece | 1–2 | Super League · Greece |
| 1999-01-18 | GenkvOostendePro League · Belgium | 3–0 | Pro League · Belgium |
| 1999-01-17 | EspanolvSociedadLa Liga · Spain | 0–0 | La Liga · Spain |
| 1999-01-17 | FarensevSalgueirosPrimeira Liga · Portugal | 2–1 | Primeira Liga · Portugal |
| 1999-01-17 | TorinovF. AndriaSerie B · Italy | 2–0 | Serie B · Italy |
| 1999-01-17 | SalernitanavPiacenzaSerie A · Italy | 1–1 | Serie A · Italy |
| 1999-01-17 | AtalantavTrevisoSerie B · Italy | 2–2 | Serie B · Italy |
| 1999-01-17 | CharltonvNewcastlePremier League · England | 2–2 | Premier League · England |
| 1999-01-17 | FiorentinavCagliariSerie A · Italy | 4–2 | Serie A · Italy |
| 1999-01-17 | ParmavLazioSerie A · Italy | 1–3 | Serie A · Italy |
| 1999-01-17 | Real MadridvAth MadridLa Liga · Spain | 4–2 | La Liga · Spain |
| 1999-01-17 | BetisvBarcelonaLa Liga · Spain | 0–3 | La Liga · Spain |
| 1999-01-17 | PAOKvProodeytikiSuper League · Greece | 1–0 | Super League · Greece |
| 1999-01-17 | MilanvPerugiaSerie A · Italy | 2–1 | Serie A · Italy |
| 1999-01-17 | MalagavToledoLa Liga 2 · Spain | 3–0 | La Liga 2 · Spain |
| 1999-01-17 | SunderlandvIpswichChampionship · England | 2–1 | Championship · England |
| 1999-01-17 | Beira MarvSp BragaPrimeira Liga · Portugal | 4–2 | Primeira Liga · Portugal |
| 1999-01-17 | PanioniosvEthnikos AsterasSuper League · Greece | 2–0 | Super League · Greece |
| 1999-01-17 | Ath Madrid BvBadajozLa Liga 2 · Spain | 1–1 | La Liga 2 · Spain |
| 1999-01-17 | AlavesvAth BilbaoLa Liga · Spain | 1–2 | La Liga · Spain |
| 1999-01-17 | GuimaraesvBoavistaPrimeira Liga · Portugal | 2–3 | Primeira Liga · Portugal |
| 1999-01-17 | ZaragozavValladolidLa Liga · Spain | 2–0 | La Liga · Spain |
| 1999-01-17 | MaritimovLeiriaPrimeira Liga · Portugal | 3–2 | Primeira Liga · Portugal |
| 1999-01-17 | OlympiakosvXanthiSuper League · Greece | 3–1 | Super League · Greece |
| 1999-01-17 | AEKvIraklisSuper League · Greece | 2–2 | Super League · Greece |
| 1999-01-17 | BarivSampdoriaSerie A · Italy | 3–1 | Serie A · Italy |
| 1999-01-17 | Las PalmasvHerculesLa Liga 2 · Spain | 4–2 | La Liga 2 · Spain |
| 1999-01-17 | ValencevWasquehalLigue 2 · France | 2–0 | Ligue 2 · France |
| 1999-01-17 | LavalvNimesLigue 2 · France | 2–1 | Ligue 2 · France |
| 1999-01-17 | VeneziavJuventusSerie A · Italy | 1–1 | Serie A · Italy |
| 1999-01-17 | KortrijkvLiersePro League · Belgium | 3–2 | Pro League · Belgium |
| 1999-01-17 | CompostelavSevillaLa Liga 2 · Spain | 1–0 | La Liga 2 · Spain |
| 1999-01-17 | SantandervVillarealLa Liga · Spain | 1–2 | La Liga · Spain |
| 1999-01-17 | ExtremaduravLa CorunaLa Liga · Spain | 1–2 | La Liga · Spain |
| 1999-01-17 | GenoavCesenaSerie B · Italy | 4–1 | Serie B · Italy |
| 1999-01-17 | GueugnonvNiortLigue 2 · France | 1–1 | Ligue 2 · France |
| 1999-01-17 | MetzvStrasbourgLigue 1 · France | 1–0 | Ligue 1 · France |
| 1999-01-17 | Sp GijonvBarcelona BLa Liga 2 · Spain | 2–1 | La Liga 2 · Spain |
| 1999-01-17 | PescaravLecceSerie B · Italy | 0–0 | Serie B · Italy |
| 1999-01-17 | NumanciavOurenseLa Liga 2 · Spain | 4–0 | La Liga 2 · Spain |