| 1999-01-16 | BerwickvStenhousemuirLeague Two · Scotland | 2–1 | League Two · Scotland |
| 1999-01-16 | CeltavMallorcaLa Liga · Spain | 4–2 | La Liga · Spain |
| 1999-01-16 | GillinghamvYorkLeague One · England | 3–1 | League One · England |
| 1999-01-16 | AyrvAirdrieChampionship · Scotland | 0–1 | Championship · Scotland |
| 1999-01-16 | St EtiennevCannesLigue 2 · France | 6–1 | Ligue 2 · France |
| 1999-01-16 | RotherhamvLeyton OrientLeague Two · England | 3–1 | League Two · England |
| 1999-01-16 | TorquayvRochdaleLeague Two · England | 2–1 | League Two · England |
| 1999-01-16 | ChelseavCoventryPremier League · England | 2–1 | Premier League · England |
| 1999-01-16 | HartlepoolvBarnetLeague Two · England | 2–2 | League Two · England |
| 1999-01-16 | HibernianvHamiltonChampionship · Scotland | 4–0 | Championship · Scotland |
| 1999-01-16 | RennesvMarseilleLigue 1 · France | 1–1 | Ligue 1 · France |
| 1999-01-16 | Le HavrevBastiaLigue 1 · France | 1–1 | Ligue 1 · France |
| 1999-01-16 | PartickvArbroathLeague One · Scotland | 0–0 | League One · Scotland |
| 1999-01-16 | CharleroivLokerenPro League · Belgium | 2–1 | Pro League · Belgium |
| 1999-01-16 | Nott'm ForestvArsenalPremier League · England | 0–1 | Premier League · England |
| 1999-01-16 | Man CityvFulhamLeague One · England | 3–0 | League One · England |
| 1999-01-16 | LleidavRecreativoLa Liga 2 · Spain | 0–2 | La Liga 2 · Spain |
| 1999-01-16 | Red Star 93vTroyesLigue 2 · France | 2–2 | Ligue 2 · France |
| 1999-01-16 | MontpelliervBordeauxLigue 1 · France | 1–1 | Ligue 1 · France |
| 1999-01-16 | WesterlovLommelPro League · Belgium | 2–1 | Pro League · Belgium |
| 1999-01-16 | StranraervRaith RvsChampionship · Scotland | 2–0 | Championship · Scotland |
| 1999-01-16 | LiverpoolvSouthamptonPremier League · England | 7–1 | Premier League · England |
| 1999-01-16 | AjacciovCaenLigue 2 · France | 2–1 | Ligue 2 · France |
| 1999-01-16 | PrestonvLutonLeague One · England | 2–1 | League One · England |
| 1999-01-16 | LeedsvMiddlesbroughPremier League · England | 2–0 | Premier League · England |
| 1999-01-16 | PlymouthvMansfieldLeague Two · England | 3–0 | League Two · England |
| 1999-01-16 | BradfordvCreweChampionship · England | 4–1 | Championship · England |
| 1999-01-16 | Bristol CityvTranmereChampionship · England | 1–1 | Championship · England |
| 1999-01-16 | BournemouthvNotts CountyLeague One · England | 2–0 | League One · England |
| 1999-01-16 | GentvStandardPro League · Belgium | 3–2 | Pro League · Belgium |
| 1999-01-16 | NorwichvWest BromChampionship · England | 1–1 | Championship · England |
| 1999-01-16 | BuryvQPRChampionship · England | 1–1 | Championship · England |
| 1999-01-16 | ArisvOFISuper League · Greece | 3–1 | Super League · Greece |
| 1999-01-16 | Port ValevSwindonChampionship · England | 0–1 | Championship · England |
| 1999-01-16 | BurnleyvChesterfieldLeague One · England | 1–2 | League One · England |
| 1999-01-16 | ClydevInverness CLeague One · Scotland | 1–1 | League One · Scotland |
| 1999-01-16 | NicevLe MansLigue 2 · France | 2–0 | Ligue 2 · France |
| 1999-01-16 | ForfarvStirlingLeague One · Scotland | 3–3 | League One · Scotland |
| 1999-01-16 | LillevBeauvaisLigue 2 · France | 1–0 | Ligue 2 · France |
| 1999-01-16 | East StirlingvQueens ParkLeague Two · Scotland | 1–1 | League Two · Scotland |
| 1999-01-16 | Est AmadoravBenficaPrimeira Liga · Portugal | 0–1 | Primeira Liga · Portugal |
| 1999-01-16 | AlloavLivingstonLeague One · Scotland | 1–3 | League One · Scotland |
| 1999-01-15 | ChestervBrightonLeague Two · England | 1–1 | League Two · England |
| 1999-01-15 | ColchestervWrexhamLeague One · England | 1–3 | League One · England |
| 1999-01-15 |  Burkina Fasov MaliFriendly | 4–1 | Friendly |
| 1999-01-15 | Sp LisbonvSetubalPrimeira Liga · Portugal | 0–0 | Primeira Liga · Portugal |
| 1999-01-15 | MouscronvAnderlechtPro League · Belgium | 2–3 | Pro League · Belgium |
| 1999-01-14 |  Bermudav Antigua and BarbudaFriendly | 0–1 | Friendly |
| 1999-01-13 | StandardvLiersePro League · Belgium | 2–2 | Pro League · Belgium |
| 1999-01-13 | PartickvAlloaLeague One · Scotland | 2–1 | League One · Scotland |