| 1999-12-05 | UnterhachingvBielefeldBundesliga · Germany | 2–0 | Bundesliga · Germany |
| 1999-12-05 | ErzurumsporvAntalyasporSüper Lig · Türkiye | 4–0 | Süper Lig · Türkiye |
| 1999-12-05 | DerbyvLeedsPremier League · England | 0–1 | Premier League · England |
| 1999-12-05 | IntervUdineseSerie A · Italy | 3–0 | Serie A · Italy |
| 1999-12-05 | PescaravRavennaSerie B · Italy | 1–2 | Serie B · Italy |
| 1999-12-05 | AltayvIstanbulsporSüper Lig · Türkiye | 0–0 | Süper Lig · Türkiye |
| 1999-12-05 | LevantevLeganesLaLiga 2 · Spain | 5–2 | LaLiga 2 · Spain |
| 1999-12-05 | VeneziavRegginaSerie A · Italy | 2–0 | Serie A · Italy |
| 1999-12-05 | CesenavBresciaSerie B · Italy | 2–2 | Serie B · Italy |
| 1999-12-05 | GaziantepsporvKocaelisporSüper Lig · Türkiye | 1–0 | Süper Lig · Türkiye |
| 1999-12-05 | LiverpoolvSheffield WedsPremier League · England | 4–1 | Premier League · England |
| 1999-12-05 | VansporvTrabzonsporSüper Lig · Türkiye | 2–2 | Süper Lig · Türkiye |
| 1999-12-05 | BadajozvLogronesLaLiga 2 · Spain | 2–1 | LaLiga 2 · Spain |
| 1999-12-05 | VicenzavSampdoriaSerie B · Italy | 2–1 | Serie B · Italy |
| 1999-12-05 | CampomaiorensevSalgueirosPrimeira Liga · Portugal | 0–1 | Primeira Liga · Portugal |
| 1999-12-05 | LeiriavMaritimoPrimeira Liga · Portugal | 0–1 | Primeira Liga · Portugal |
| 1999-12-04 | PrestonvOldhamLeague One · England | 2–0 | League One · England |
| 1999-12-04 | HartlepoolvPeterboroLeague Two · England | 1–0 | League Two · England |
| 1999-12-04 | WrexhamvBlackpoolLeague One · England | 1–1 | League One · England |
| 1999-12-04 | SpartavFeyenoordEredivisie · Netherlands | 1–3 | Eredivisie · Netherlands |
| 1999-12-04 | Bayern MunichvDortmundBundesliga · Germany | 1–1 | Bundesliga · Germany |
| 1999-12-04 | PSV EindhovenvRoda JCEredivisie · Netherlands | 2–0 | Eredivisie · Netherlands |
| 1999-12-04 | BeverenvLokerenPro League · Belgium | 2–1 | Pro League · Belgium |
| 1999-12-04 | For SittardvDen BoschEredivisie · Netherlands | 1–1 | Eredivisie · Netherlands |
| 1999-12-04 | MillwallvCardiffLeague One · England | 2–0 | League One · England |
| 1999-12-04 | LeverkusenvWerder BremenBundesliga · Germany | 3–2 | Bundesliga · Germany |
| 1999-12-04 | BurnleyvWycombeLeague One · England | 1–0 | League One · England |
| 1999-12-04 | MannheimvCottbus2. Bundesliga · Germany | 2–1 | 2. Bundesliga · Germany |
| 1999-12-04 | Gambiav Sierra LeoneFriendly | 0–0 | Friendly |
| 1999-12-04 | BarnetvChesterLeague Two · England | 2–0 | League Two · England |
| 1999-12-04 | Schalke 04vFreiburgBundesliga · Germany | 2–2 | Bundesliga · Germany |
| 1999-12-04 | StockportvGrimsbyChampionship · England | 2–1 | Championship · England |
| 1999-12-04 | Malawiv LibyaFriendly | 1–2 | Friendly |
| 1999-12-04 | MouscronvGerminalPro League · Belgium | 1–1 | Pro League · Belgium |
| 1999-12-04 | DarlingtonvHalifaxLeague Two · England | 4–0 | League Two · England |
| 1999-12-04 | Le MansvCreteilLigue 2 · France | 2–0 | Ligue 2 · France |
| 1999-12-04 | RochdalevCheltenhamLeague Two · England | 0–0 | League Two · England |
| 1999-12-04 | CaenvNiortLigue 2 · France | 2–1 | Ligue 2 · France |
| 1999-12-04 | ValenciavSevillaLaLiga · Spain | 2–0 | LaLiga · Spain |
| 1999-12-04 | HamiltonvClydeLeague One · Scotland | 2–3 | League One · Scotland |
| 1999-12-04 | GeelvWesterloPro League · Belgium | 2–3 | Pro League · Belgium |
| 1999-12-04 | HuddersfieldvQPRChampionship · England | 1–0 | Championship · England |
| 1999-12-04 | GillinghamvBuryLeague One · England | 1–0 | League One · England |
| 1999-12-04 | Real MadridvZaragozaLaLiga · Spain | 1–5 | LaLiga · Spain |
| 1999-12-04 | StuttgartvMunich 1860Bundesliga · Germany | 1–3 | Bundesliga · Germany |
| 1999-12-04 | SouthamptonvCoventryPremier League · England | 0–0 | Premier League · England |
| 1999-12-04 | BradfordvMiddlesbroughPremier League · England | 1–1 | Premier League · England |
| 1999-12-04 | Raith RvsvInverness CChampionship · Scotland | 4–2 | Championship · Scotland |
| 1999-12-04 | WimbledonvWatfordPremier League · England | 5–0 | Premier League · England |
| 1999-12-04 | GuimaraesvSp LisbonPrimeira Liga · Portugal | 1–2 | Primeira Liga · Portugal |