| 1999-12-28 | BarnetvHalifaxLeague Two · England | 0–1 | League Two · England |
| 1999-12-26 | HalifaxvLincolnLeague Two · England | 3–0 | League Two · England |
| 1999-12-18 | ChestervHalifaxLeague Two · England | 2–1 | League Two · England |
| 1999-12-11 | HalifaxvRotherhamLeague Two · England | 0–0 | League Two · England |
| 1999-12-04 | DarlingtonvHalifaxLeague Two · England | 4–0 | League Two · England |
| 1999-11-27 | HalifaxvMansfieldLeague Two · England | 0–1 | League Two · England |
| 1999-11-23 | HullvHalifaxLeague Two · England | 0–1 | League Two · England |
| 1999-11-12 | HalifaxvExeterLeague Two · England | 1–0 | League Two · England |
| 1999-11-05 | SwanseavHalifaxLeague Two · England | 3–1 | League Two · England |
| 1999-11-02 | HalifaxvCheltenhamLeague Two · England | 1–1 | League Two · England |
| 1999-10-23 | CarlislevHalifaxLeague Two · England | 1–1 | League Two · England |
| 1999-10-19 | HalifaxvYorkLeague Two · England | 0–2 | League Two · England |
| 1999-10-16 | HalifaxvPeterboroLeague Two · England | 2–1 | League Two · England |
| 1999-10-09 | MacclesfieldvHalifaxLeague Two · England | 0–2 | League Two · England |
| 1999-10-02 | ShrewsburyvHalifaxLeague Two · England | 0–0 | League Two · England |
| 1999-09-25 | HalifaxvCarlisleLeague Two · England | 5–2 | League Two · England |
| 1999-09-18 | SouthendvHalifaxLeague Two · England | 4–1 | League Two · England |
| 1999-09-11 | HalifaxvBrightonLeague Two · England | 2–1 | League Two · England |
| 1999-09-03 | RochdalevHalifaxLeague Two · England | 0–1 | League Two · England |
| 1999-08-31 | HalifaxvTorquayLeague Two · England | 2–0 | League Two · England |
| 1999-08-28 | Leyton OrientvHalifaxLeague Two · England | 1–0 | League Two · England |
| 1999-08-21 | HalifaxvPlymouthLeague Two · England | 0–1 | League Two · England |
| 1999-08-14 | HartlepoolvHalifaxLeague Two · England | 0–2 | League Two · England |
| 1999-08-07 | HalifaxvDarlingtonLeague Two · England | 0–1 | League Two · England |
| 1999-05-08 | ExetervHalifaxLeague Two · England | 2–1 | League Two · England |
| 1999-05-01 | HalifaxvScarboroughLeague Two · England | 1–2 | League Two · England |
| 1999-04-27 | HalifaxvScunthorpeLeague Two · England | 1–0 | League Two · England |
| 1999-04-24 | ChestervHalifaxLeague Two · England | 2–2 | League Two · England |
| 1999-04-17 | HalifaxvBrightonLeague Two · England | 1–0 | League Two · England |
| 1999-04-13 | MansfieldvHalifaxLeague Two · England | 0–1 | League Two · England |
| 1999-04-10 | CambridgevHalifaxLeague Two · England | 4–0 | League Two · England |
| 1999-04-05 | HalifaxvRochdaleLeague Two · England | 0–0 | League Two · England |
| 1999-04-03 | BarnetvHalifaxLeague Two · England | 2–2 | League Two · England |
| 1999-03-26 | HalifaxvLeyton OrientLeague Two · England | 1–2 | League Two · England |
| 1999-03-20 | SwanseavHalifaxLeague Two · England | 1–2 | League Two · England |
| 1999-03-16 | BrentfordvHalifaxLeague Two · England | 1–1 | League Two · England |
| 1999-03-13 | HalifaxvCarlisleLeague Two · England | 1–0 | League Two · England |
| 1999-03-06 | TorquayvHalifaxLeague Two · England | 4–0 | League Two · England |
| 1999-02-27 | HalifaxvHullLeague Two · England | 0–1 | League Two · England |
| 1999-02-19 | CardiffvHalifaxLeague Two · England | 1–1 | League Two · England |
| 1999-02-13 | HalifaxvSouthendLeague Two · England | 3–1 | League Two · England |
| 1999-02-06 | HartlepoolvHalifaxLeague Two · England | 2–0 | League Two · England |
| 1999-01-30 | HalifaxvRotherhamLeague Two · England | 2–4 | League Two · England |
| 1999-01-23 | HalifaxvPlymouthLeague Two · England | 2–0 | League Two · England |
| 1999-01-09 | HalifaxvPeterboroLeague Two · England | 2–2 | League Two · England |
| 1999-01-02 | ShrewsburyvHalifaxLeague Two · England | 2–2 | League Two · England |