| 1999-05-08 | ScarboroughvPeterboroLeague Two · England | 1–1 | League Two · England |
| 1999-05-05 | ScarboroughvPlymouthLeague Two · England | 3–0 | League Two · England |
| 1999-05-01 | HalifaxvScarboroughLeague Two · England | 1–2 | League Two · England |
| 1999-04-24 | ScarboroughvCardiffLeague Two · England | 1–2 | League Two · England |
| 1999-04-21 | ScarboroughvLeyton OrientLeague Two · England | 1–3 | League Two · England |
| 1999-04-17 | HartlepoolvScarboroughLeague Two · England | 3–0 | League Two · England |
| 1999-04-14 | ScarboroughvDarlingtonLeague Two · England | 0–2 | League Two · England |
| 1999-04-10 | BarnetvScarboroughLeague Two · England | 1–0 | League Two · England |
| 1999-04-05 | ScarboroughvCarlisleLeague Two · England | 3–0 | League Two · England |
| 1999-04-03 | HullvScarboroughLeague Two · England | 1–1 | League Two · England |
| 1999-03-26 | ScarboroughvRochdaleLeague Two · England | 1–0 | League Two · England |
| 1999-03-20 | TorquayvScarboroughLeague Two · England | 0–1 | League Two · England |
| 1999-03-13 | ScarboroughvRotherhamLeague Two · England | 0–4 | League Two · England |
| 1999-03-09 | ChestervScarboroughLeague Two · England | 1–3 | League Two · England |
| 1999-02-27 | BrentfordvScarboroughLeague Two · England | 1–1 | League Two · England |
| 1999-02-20 | ScarboroughvSwanseaLeague Two · England | 2–1 | League Two · England |
| 1999-02-13 | ShrewsburyvScarboroughLeague Two · England | 3–1 | League Two · England |
| 1999-02-06 | ScarboroughvCambridgeLeague Two · England | 1–5 | League Two · England |
| 1999-01-30 | ScunthorpevScarboroughLeague Two · England | 5–1 | League Two · England |
| 1999-01-23 | BrightonvScarboroughLeague Two · England | 1–0 | League Two · England |
| 1999-01-16 | ScarboroughvExeterLeague Two · England | 1–0 | League Two · England |
| 1999-01-09 | SouthendvScarboroughLeague Two · England | 1–0 | League Two · England |