| 1999-12-28 | LincolnvHartlepoolLeague Two · England | 1–2 | League Two · England |
| 1999-12-26 | HartlepoolvYorkLeague Two · England | 2–1 | League Two · England |
| 1999-12-18 | ExetervHartlepoolLeague Two · England | 1–2 | League Two · England |
| 1999-12-11 | HartlepoolvSwanseaLeague Two · England | 0–1 | League Two · England |
| 1999-12-04 | HartlepoolvPeterboroLeague Two · England | 1–0 | League Two · England |
| 1999-11-27 | MacclesfieldvHartlepoolLeague Two · England | 3–3 | League Two · England |
| 1999-11-23 | TorquayvHartlepoolLeague Two · England | 0–0 | League Two · England |
| 1999-11-13 | HartlepoolvChesterLeague Two · England | 1–0 | League Two · England |
| 1999-11-06 | BrightonvHartlepoolLeague Two · England | 1–0 | League Two · England |
| 1999-11-02 | HartlepoolvBarnetLeague Two · England | 3–0 | League Two · England |
| 1999-10-23 | HartlepoolvLeyton OrientLeague Two · England | 1–0 | League Two · England |
| 1999-10-19 | RotherhamvHartlepoolLeague Two · England | 3–0 | League Two · England |
| 1999-10-16 | MansfieldvHartlepoolLeague Two · England | 2–3 | League Two · England |
| 1999-10-09 | HartlepoolvHullLeague Two · England | 2–0 | League Two · England |
| 1999-10-02 | HartlepoolvDarlingtonLeague Two · England | 2–0 | League Two · England |
| 1999-09-25 | Leyton OrientvHartlepoolLeague Two · England | 2–1 | League Two · England |
| 1999-09-18 | HartlepoolvPlymouthLeague Two · England | 3–0 | League Two · England |
| 1999-09-11 | NorthamptonvHartlepoolLeague Two · England | 2–1 | League Two · England |
| 1999-09-04 | HartlepoolvSouthendLeague Two · England | 1–2 | League Two · England |
| 1999-08-31 | ShrewsburyvHartlepoolLeague Two · England | 0–0 | League Two · England |
| 1999-08-28 | HartlepoolvCheltenhamLeague Two · England | 0–1 | League Two · England |
| 1999-08-21 | CarlislevHartlepoolLeague Two · England | 0–3 | League Two · England |
| 1999-08-14 | HartlepoolvHalifaxLeague Two · England | 0–2 | League Two · England |
| 1999-08-07 | PeterborovHartlepoolLeague Two · England | 2–1 | League Two · England |
| 1999-05-08 | SouthendvHartlepoolLeague Two · England | 1–1 | League Two · England |
| 1999-05-01 | HartlepoolvCarlisleLeague Two · England | 0–0 | League Two · England |
| 1999-04-27 | HartlepoolvLeyton OrientLeague Two · England | 1–0 | League Two · England |
| 1999-04-24 | MansfieldvHartlepoolLeague Two · England | 2–0 | League Two · England |
| 1999-04-17 | HartlepoolvScarboroughLeague Two · England | 3–0 | League Two · England |
| 1999-04-13 | SwanseavHartlepoolLeague Two · England | 1–0 | League Two · England |
| 1999-04-10 | HartlepoolvChesterLeague Two · England | 2–0 | League Two · England |
| 1999-04-06 | ShrewsburyvHartlepoolLeague Two · England | 0–1 | League Two · England |
| 1999-04-03 | HartlepoolvBrentfordLeague Two · England | 0–1 | League Two · England |
| 1999-03-27 | TorquayvHartlepoolLeague Two · England | 3–0 | League Two · England |
| 1999-03-20 | HartlepoolvBrightonLeague Two · England | 0–0 | League Two · England |
| 1999-03-13 | PlymouthvHartlepoolLeague Two · England | 0–0 | League Two · England |
| 1999-03-06 | PeterborovHartlepoolLeague Two · England | 1–1 | League Two · England |
| 1999-02-27 | HartlepoolvRotherhamLeague Two · England | 0–0 | League Two · England |
| 1999-02-20 | ExetervHartlepoolLeague Two · England | 2–1 | League Two · England |
| 1999-02-13 | HartlepoolvDarlingtonLeague Two · England | 2–3 | League Two · England |
| 1999-02-06 | HartlepoolvHalifaxLeague Two · England | 2–0 | League Two · England |
| 1999-01-30 | RochdalevHartlepoolLeague Two · England | 0–1 | League Two · England |
| 1999-01-23 | HullvHartlepoolLeague Two · England | 4–0 | League Two · England |
| 1999-01-16 | HartlepoolvBarnetLeague Two · England | 2–2 | League Two · England |
| 1999-01-09 | CardiffvHartlepoolLeague Two · England | 4–1 | League Two · England |
| 1999-01-02 | HartlepoolvCambridgeLeague Two · England | 2–2 | League Two · England |