| 1999-12-18 | RotherhamvDarlingtonLeague Two · England | 2–1 | League Two · England |
| 1999-12-11 | HalifaxvRotherhamLeague Two · England | 0–0 | League Two · England |
| 1999-12-04 | RotherhamvLincolnLeague Two · England | 1–1 | League Two · England |
| 1999-11-27 | CarlislevRotherhamLeague Two · England | 0–1 | League Two · England |
| 1999-11-23 | MansfieldvRotherhamLeague Two · England | 1–2 | League Two · England |
| 1999-11-12 | RotherhamvLeyton OrientLeague Two · England | 0–1 | League Two · England |
| 1999-11-06 | HullvRotherhamLeague Two · England | 0–0 | League Two · England |
| 1999-11-02 | RotherhamvTorquayLeague Two · England | 1–0 | League Two · England |
| 1999-10-23 | NorthamptonvRotherhamLeague Two · England | 0–1 | League Two · England |
| 1999-10-19 | RotherhamvHartlepoolLeague Two · England | 3–0 | League Two · England |
| 1999-10-16 | RotherhamvBarnetLeague Two · England | 2–0 | League Two · England |
| 1999-10-12 | SwanseavRotherhamLeague Two · England | 2–0 | League Two · England |
| 1999-10-02 | CheltenhamvRotherhamLeague Two · England | 0–2 | League Two · England |
| 1999-09-25 | RotherhamvNorthamptonLeague Two · England | 3–0 | League Two · England |
| 1999-09-18 | RotherhamvRochdaleLeague Two · England | 0–1 | League Two · England |
| 1999-09-11 | PlymouthvRotherhamLeague Two · England | 1–1 | League Two · England |
| 1999-09-04 | RotherhamvYorkLeague Two · England | 1–0 | League Two · England |
| 1999-08-30 | MacclesfieldvRotherhamLeague Two · England | 1–1 | League Two · England |
| 1999-08-28 | RotherhamvShrewsburyLeague Two · England | 4–0 | League Two · England |
| 1999-08-21 | ExetervRotherhamLeague Two · England | 3–1 | League Two · England |
| 1999-08-14 | RotherhamvChesterLeague Two · England | 4–0 | League Two · England |
| 1999-08-07 | LincolnvRotherhamLeague Two · England | 2–1 | League Two · England |
| 1999-05-08 | ChestervRotherhamLeague Two · England | 1–1 | League Two · England |
| 1999-05-01 | RotherhamvBrightonLeague Two · England | 2–1 | League Two · England |
| 1999-04-27 | RotherhamvBarnetLeague Two · England | 1–1 | League Two · England |
| 1999-04-24 | TorquayvRotherhamLeague Two · England | 2–0 | League Two · England |
| 1999-04-20 | ShrewsburyvRotherhamLeague Two · England | 2–3 | League Two · England |
| 1999-04-17 | RotherhamvCarlisleLeague Two · England | 3–1 | League Two · England |
| 1999-04-13 | ExetervRotherhamLeague Two · England | 3–0 | League Two · England |
| 1999-04-10 | RochdalevRotherhamLeague Two · England | 0–0 | League Two · England |
| 1999-04-05 | RotherhamvSwanseaLeague Two · England | 1–0 | League Two · England |
| 1999-04-03 | DarlingtonvRotherhamLeague Two · England | 1–2 | League Two · England |
| 1999-03-27 | RotherhamvScunthorpeLeague Two · England | 0–0 | League Two · England |
| 1999-03-20 | RotherhamvPeterboroLeague Two · England | 2–2 | League Two · England |
| 1999-03-16 | RotherhamvCardiffLeague Two · England | 1–0 | League Two · England |
| 1999-03-13 | ScarboroughvRotherhamLeague Two · England | 0–4 | League Two · England |
| 1999-02-27 | HartlepoolvRotherhamLeague Two · England | 0–0 | League Two · England |
| 1999-02-20 | RotherhamvBrentfordLeague Two · England | 2–4 | League Two · England |
| 1999-02-13 | PlymouthvRotherhamLeague Two · England | 1–0 | League Two · England |
| 1999-02-06 | RotherhamvSouthendLeague Two · England | 2–2 | League Two · England |
| 1999-01-30 | HalifaxvRotherhamLeague Two · England | 2–4 | League Two · England |
| 1999-01-22 | MansfieldvRotherhamLeague Two · England | 0–3 | League Two · England |
| 1999-01-16 | RotherhamvLeyton OrientLeague Two · England | 3–1 | League Two · England |
| 1999-01-09 | HullvRotherhamLeague Two · England | 1–0 | League Two · England |
| 1998-12-28 | RotherhamvHalifaxLeague Two · England | 3–1 | League Two · England |
| 1998-12-26 | CambridgevRotherhamLeague Two · England | 3–2 | League Two · England |
| 1998-12-18 | RotherhamvChesterLeague Two · England | 2–4 | League Two · England |
| 1998-12-12 | BrightonvRotherhamLeague Two · England | 4–1 | League Two · England |
| 1998-11-28 | RotherhamvExeterLeague Two · England | 0–0 | League Two · England |
| 1998-11-21 | CarlislevRotherhamLeague Two · England | 0–0 | League Two · England |