| 1999-01-30 | YorkvOldhamLeague One · England | 0–1 | League One · England |
| 1999-01-30 | AirdrievHibernianChampionship · Scotland | 1–4 | Championship · Scotland |
| 1999-01-30 | StrasbourgvLe HavreLigue 1 · France | 0–1 | Ligue 1 · France |
| 1999-01-30 | WatfordvSunderlandChampionship · England | 2–1 | Championship · England |
| 1999-01-30 | CaenvAmiensLigue 2 · France | 0–0 | Ligue 2 · France |
| 1999-01-30 | NimesvRed Star 93Ligue 2 · France | 2–0 | Ligue 2 · France |
| 1999-01-30 | CrewevSheffield UnitedChampionship · England | 1–2 | Championship · England |
| 1999-01-30 | St TruidenvAalstPro League · Belgium | 2–0 | Pro League · Belgium |
| 1999-01-30 | BarnetvSwanseaLeague Two · England | 0–1 | League Two · England |
| 1999-01-30 | OxfordvBarnsleyChampionship · England | 1–0 | Championship · England |
| 1999-01-30 | Sheffield WedsvDerbyPremier League · England | 0–1 | Premier League · England |
| 1999-01-30 | TranmerevCrystal PalaceChampionship · England | 3–1 | Championship · England |
| 1999-01-30 | WasquehalvChateaurouxLigue 2 · France | 1–0 | Ligue 2 · France |
| 1999-01-30 | BlackpoolvMacclesfieldLeague One · England | 2–1 | League One · England |
| 1999-01-30 | SedanvLavalLigue 2 · France | 1–0 | Ligue 2 · France |
| 1999-01-30 | NiortvValenceLigue 2 · France | 1–0 | Ligue 2 · France |
| 1999-01-30 | ExetervPlymouthLeague Two · England | 1–1 | League Two · England |
| 1999-01-30 | WalsallvWiganLeague One · England | 1–2 | League One · England |
| 1999-01-30 | Ath BilbaovZaragozaLa Liga · Spain | 2–0 | La Liga · Spain |
| 1999-01-30 | BrechinvBerwickLeague Two · Scotland | 0–3 | League Two · Scotland |
| 1999-01-30 | KilmarnockvDundeePremiership · Scotland | 0–0 | Premiership · Scotland |
| 1999-01-30 | Barcelona BvMallorca BLa Liga 2 · Spain | 1–2 | La Liga 2 · Spain |
| 1999-01-30 | Bristol RvsvColchesterLeague One · England | 1–1 | League One · England |
| 1999-01-30 | East StirlingvMontroseLeague Two · Scotland | 2–1 | League Two · Scotland |
| 1999-01-30 | ChievovTrevisoSerie B · Italy | 4–2 | Serie B · Italy |
| 1999-01-30 | SwindonvBuryChampionship · England | 1–1 | Championship · England |
| 1999-01-30 | LincolnvBurnleyLeague One · England | 1–1 | League One · England |
| 1999-01-30 | OviedovSociedadLa Liga · Spain | 2–1 | La Liga · Spain |
| 1999-01-30 | Queen of SthvAlloaLeague One · Scotland | 0–0 | League One · Scotland |
| 1999-01-30 | WrexhamvPrestonLeague One · England | 0–5 | League One · England |
| 1999-01-29 | Club BruggevAnderlechtPro League · Belgium | 2–0 | Pro League · Belgium |
| 1999-01-29 | BastiavRennesLigue 1 · France | 0–1 | Ligue 1 · France |
| 1999-01-29 | AnkaragucuvBesiktasSüper Lig · Turkey | 0–1 | Süper Lig · Turkey |
| 1999-01-29 | Beira MarvBenficaPrimeira Liga · Portugal | 1–1 | Primeira Liga · Portugal |
| 1999-01-29 | StokevMan CityLeague One · England | 0–1 | League One · England |
| 1999-01-29 |  MonacovParis SGLigue 1 · France | 2–1 | Ligue 1 · France |
| 1999-01-29 | BordeauxvMarseilleLigue 1 · France | 4–1 | Ligue 1 · France |
| 1999-01-29 |  Vietnamv SingaporeFriendly | 1–0 | Friendly |
| 1999-01-28 |  Costa Ricav EcuadorFriendly | 0–0 | Friendly |
| 1999-01-27 | DundeevRangersPremiership · Scotland | 0–4 | Premiership · Scotland |
| 1999-01-27 |  Maltav Bosnia and HerzegovinaFriendly | 2–1 | Friendly |
| 1999-01-27 | StandardvGenkPro League · Belgium | 2–4 | Pro League · Belgium |
| 1999-01-27 | BerwickvRoss CountyLeague Two · Scotland | 2–2 | League Two · Scotland |
| 1999-01-26 | CowdenbeathvBrechinLeague Two · Scotland | 0–2 | League Two · Scotland |
| 1999-01-26 | East StirlingvDumbartonLeague Two · Scotland | 1–2 | League Two · Scotland |
| 1999-01-26 | Queens ParkvStenhousemuirLeague Two · Scotland | 4–1 | League Two · Scotland |
| 1999-01-26 | StirlingvQueen of SthLeague One · Scotland | 1–3 | League One · Scotland |
| 1999-01-26 | PeterborovHullLeague Two · England | 1–1 | League Two · England |
| 1999-01-26 | MacclesfieldvMillwallLeague One · England | 0–2 | League One · England |
| 1999-01-26 | FulhamvOldhamLeague One · England | 1–0 | League One · England |