| 1999-12-28 | NorthamptonvDarlingtonLeague Two · England | 0–3 | League Two · England |
| 1999-12-26 | DarlingtonvHullLeague Two · England | 0–0 | League Two · England |
| 1999-12-18 | RotherhamvDarlingtonLeague Two · England | 2–1 | League Two · England |
| 1999-12-15 | DarlingtonvChesterLeague Two · England | 3–1 | League Two · England |
| 1999-12-04 | DarlingtonvHalifaxLeague Two · England | 4–0 | League Two · England |
| 1999-11-27 | SouthendvDarlingtonLeague Two · England | 1–2 | League Two · England |
| 1999-11-23 | SwanseavDarlingtonLeague Two · England | 0–0 | League Two · England |
| 1999-11-12 | DarlingtonvTorquayLeague Two · England | 1–1 | League Two · England |
| 1999-11-06 | BarnetvDarlingtonLeague Two · England | 1–0 | League Two · England |
| 1999-11-02 | DarlingtonvLeyton OrientLeague Two · England | 3–1 | League Two · England |
| 1999-10-23 | PlymouthvDarlingtonLeague Two · England | 0–0 | League Two · England |
| 1999-10-19 | DarlingtonvCarlisleLeague Two · England | 3–1 | League Two · England |
| 1999-10-16 | DarlingtonvCheltenhamLeague Two · England | 1–0 | League Two · England |
| 1999-10-09 | LincolnvDarlingtonLeague Two · England | 1–0 | League Two · England |
| 1999-10-02 | HartlepoolvDarlingtonLeague Two · England | 2–0 | League Two · England |
| 1999-09-25 | DarlingtonvPlymouthLeague Two · England | 2–0 | League Two · England |
| 1999-09-18 | DarlingtonvMansfieldLeague Two · England | 0–0 | League Two · England |
| 1999-09-11 | RochdalevDarlingtonLeague Two · England | 0–0 | League Two · England |
| 1999-09-04 | DarlingtonvExeterLeague Two · England | 1–0 | League Two · England |
| 1999-08-30 | PeterborovDarlingtonLeague Two · England | 4–2 | League Two · England |
| 1999-08-28 | DarlingtonvBrightonLeague Two · England | 1–1 | League Two · England |
| 1999-08-21 | ShrewsburyvDarlingtonLeague Two · England | 0–1 | League Two · England |
| 1999-08-14 | DarlingtonvMacclesfieldLeague Two · England | 3–0 | League Two · England |
| 1999-08-07 | HalifaxvDarlingtonLeague Two · England | 0–1 | League Two · England |
| 1999-05-08 | ScunthorpevDarlingtonLeague Two · England | 0–1 | League Two · England |
| 1999-05-04 | DarlingtonvExeterLeague Two · England | 4–0 | League Two · England |
| 1999-05-01 | DarlingtonvChesterLeague Two · England | 1–2 | League Two · England |
| 1999-04-27 | DarlingtonvBrentfordLeague Two · England | 2–2 | League Two · England |
| 1999-04-24 | CarlislevDarlingtonLeague Two · England | 3–3 | League Two · England |
| 1999-04-17 | DarlingtonvCambridgeLeague Two · England | 0–0 | League Two · England |
| 1999-04-14 | ScarboroughvDarlingtonLeague Two · England | 0–2 | League Two · England |
| 1999-04-10 | DarlingtonvTorquayLeague Two · England | 0–2 | League Two · England |
| 1999-04-05 | PeterborovDarlingtonLeague Two · England | 0–1 | League Two · England |
| 1999-04-03 | DarlingtonvRotherhamLeague Two · England | 1–2 | League Two · England |
| 1999-03-26 | ExetervDarlingtonLeague Two · England | 0–0 | League Two · England |
| 1999-03-23 | DarlingtonvCarlisleLeague Two · England | 1–1 | League Two · England |
| 1999-03-20 | DarlingtonvSouthendLeague Two · England | 2–1 | League Two · England |
| 1999-03-13 | BrightonvDarlingtonLeague Two · England | 0–4 | League Two · England |
| 1999-03-09 | SwanseavDarlingtonLeague Two · England | 2–0 | League Two · England |
| 1999-02-27 | ShrewsburyvDarlingtonLeague Two · England | 3–0 | League Two · England |
| 1999-02-20 | DarlingtonvPlymouthLeague Two · England | 1–2 | League Two · England |
| 1999-02-16 | DarlingtonvHullLeague Two · England | 0–1 | League Two · England |
| 1999-02-13 | HartlepoolvDarlingtonLeague Two · England | 2–3 | League Two · England |
| 1999-02-06 | DarlingtonvMansfieldLeague Two · England | 5–1 | League Two · England |
| 1999-01-30 | Leyton OrientvDarlingtonLeague Two · England | 3–2 | League Two · England |
| 1999-01-23 | CardiffvDarlingtonLeague Two · England | 3–2 | League Two · England |
| 1999-01-09 | BarnetvDarlingtonLeague Two · England | 3–0 | League Two · England |
| 1999-01-02 | DarlingtonvRochdaleLeague Two · England | 3–0 | League Two · England |