| 1998-12-28 | DarlingtonvLeyton OrientLeague Two · England | 1–1 | League Two · England |
| 1998-12-26 | HalifaxvDarlingtonLeague Two · England | 0–0 | League Two · England |
| 1998-12-19 | DarlingtonvScunthorpeLeague Two · England | 3–1 | League Two · England |
| 1998-12-12 | ChestervDarlingtonLeague Two · England | 1–0 | League Two · England |
| 1998-11-28 | DarlingtonvScarboroughLeague Two · England | 3–0 | League Two · England |
| 1998-11-21 | CambridgevDarlingtonLeague Two · England | 2–1 | League Two · England |
| 1998-11-07 | DarlingtonvBrightonLeague Two · England | 1–2 | League Two · England |
| 1998-10-31 | SouthendvDarlingtonLeague Two · England | 2–1 | League Two · England |
| 1998-10-20 | TorquayvDarlingtonLeague Two · England | 2–2 | League Two · England |
| 1998-10-17 | RotherhamvDarlingtonLeague Two · England | 3–1 | League Two · England |
| 1998-10-10 | DarlingtonvPeterboroLeague Two · England | 3–0 | League Two · England |
| 1998-10-03 | DarlingtonvSwanseaLeague Two · England | 2–2 | League Two · England |
| 1998-09-27 | BrentfordvDarlingtonLeague Two · England | 3–0 | League Two · England |
| 1998-09-19 | DarlingtonvShrewsburyLeague Two · England | 1–0 | League Two · England |
| 1998-09-12 | PlymouthvDarlingtonLeague Two · England | 1–2 | League Two · England |
| 1998-09-08 | DarlingtonvHartlepoolLeague Two · England | 2–0 | League Two · England |
| 1998-09-05 | MansfieldvDarlingtonLeague Two · England | 0–1 | League Two · England |
| 1998-08-31 | DarlingtonvCardiffLeague Two · England | 3–0 | League Two · England |
| 1998-08-29 | RochdalevDarlingtonLeague Two · England | 0–0 | League Two · England |
| 1998-08-22 | DarlingtonvHalifaxLeague Two · England | 2–2 | League Two · England |
| 1998-08-15 | HullvDarlingtonLeague Two · England | 1–2 | League Two · England |
| 1998-08-08 | DarlingtonvBarnetLeague Two · England | 0–2 | League Two · England |
| 1998-05-02 | CardiffvDarlingtonLeague Two · England | 0–0 | League Two · England |
| 1998-04-25 | DarlingtonvLincolnLeague Two · England | 2–2 | League Two · England |
| 1998-04-18 | ScunthorpevDarlingtonLeague Two · England | 1–0 | League Two · England |
| 1998-04-13 | DarlingtonvChesterLeague Two · England | 1–0 | League Two · England |
| 1998-04-11 | ShrewsburyvDarlingtonLeague Two · England | 3–0 | League Two · England |
| 1998-04-04 | DarlingtonvBarnetLeague Two · England | 2–3 | League Two · England |
| 1998-03-31 | DarlingtonvShrewsburyLeague Two · England | 3–1 | League Two · England |
| 1998-03-29 | CambridgevDarlingtonLeague Two · England | 1–0 | League Two · England |
| 1998-03-21 | Leyton OrientvDarlingtonLeague Two · England | 2–0 | League Two · England |
| 1998-03-14 | DarlingtonvTorquayLeague Two · England | 1–2 | League Two · England |
| 1998-03-07 | HullvDarlingtonLeague Two · England | 1–1 | League Two · England |
| 1998-03-03 | DarlingtonvPeterboroLeague Two · England | 3–1 | League Two · England |
| 1998-02-28 | DarlingtonvRochdaleLeague Two · England | 1–0 | League Two · England |
| 1998-02-24 | DoncastervDarlingtonLeague Two · England | 0–2 | League Two · England |
| 1998-02-21 | MansfieldvDarlingtonLeague Two · England | 4–0 | League Two · England |
| 1998-02-14 | DarlingtonvNotts CountyLeague Two · England | 0–2 | League Two · England |
| 1998-02-07 | HartlepoolvDarlingtonLeague Two · England | 2–2 | League Two · England |
| 1998-01-31 | DarlingtonvBrightonLeague Two · England | 1–0 | League Two · England |
| 1998-01-27 | SwanseavDarlingtonLeague Two · England | 4–0 | League Two · England |
| 1998-01-24 | DarlingtonvExeterLeague Two · England | 3–2 | League Two · England |
| 1998-01-17 | RotherhamvDarlingtonLeague Two · England | 3–0 | League Two · England |
| 1998-01-10 | DarlingtonvColchesterLeague Two · England | 4–2 | League Two · England |
| 1998-01-06 | ScarboroughvDarlingtonLeague Two · England | 2–1 | League Two · England |