| 1999-01-02 | HartlepoolvCambridgeLeague Two · England | 2–2 | League Two · England |
| 1999-01-02 | ColchestervLutonLeague One · England | 2–2 | League One · England |
| 1999-01-02 | BurnleyvWalsallLeague One · England | 0–0 | League One · England |
| 1999-01-02 | GillinghamvBlackpoolLeague One · England | 1–0 | League One · England |
| 1999-01-02 | DunfermlinevHeartsPremiership · Scotland | 0–0 | Premiership · Scotland |
| 1999-01-02 | St JohnstonevAberdeenPremiership · Scotland | 4–1 | Premiership · Scotland |
| 1999-01-02 | BrentfordvBarnetLeague Two · England | 3–1 | League Two · England |
| 1999-01-02 | ValenciavSociedadLa Liga · Spain | 2–0 | La Liga · Spain |
| 1999-01-02 | CarlislevExeterLeague Two · England | 1–3 | League Two · England |
| 1999-01-02 | ToledovBarcelona BLa Liga 2 · Spain | 2–1 | La Liga 2 · Spain |
| 1999-01-02 | Mallorca BvLeganesLa Liga 2 · Spain | 2–1 | La Liga 2 · Spain |
| 1999-01-02 | WycombevYorkLeague One · England | 1–2 | League One · England |
| 1999-01-02 | DarlingtonvRochdaleLeague Two · England | 3–0 | League Two · England |
| 1999-01-02 | DundeevDundee UnitedPremiership · Scotland | 1–3 | Premiership · Scotland |
| 1999-01-02 | FalkirkvAirdrieChampionship · Scotland | 1–1 | Championship · Scotland |
| 1999-01-02 | AyrvStranraerChampionship · Scotland | 4–0 | Championship · Scotland |
| 1999-01-02 | ShrewsburyvHalifaxLeague Two · England | 2–2 | League Two · England |
| 1999-01-01 | MotherwellvKilmarnockPremiership · Scotland | 1–2 | Premiership · Scotland |