| 1998-12-28 | HartlepoolvRochdaleLeague Two · England | 0–1 | League Two · England |
| 1998-12-26 | ScunthorpevHartlepoolLeague Two · England | 1–0 | League Two · England |
| 1998-12-19 | HartlepoolvSouthendLeague Two · England | 2–4 | League Two · England |
| 1998-12-12 | CarlislevHartlepoolLeague Two · England | 2–1 | League Two · England |
| 1998-11-28 | HartlepoolvSwanseaLeague Two · England | 1–2 | League Two · England |
| 1998-11-21 | ScarboroughvHartlepoolLeague Two · England | 1–2 | League Two · England |
| 1998-11-10 | HartlepoolvMansfieldLeague Two · England | 1–2 | League Two · England |
| 1998-11-07 | HartlepoolvPlymouthLeague Two · England | 2–0 | League Two · England |
| 1998-10-31 | BrightonvHartlepoolLeague Two · England | 3–2 | League Two · England |
| 1998-10-24 | HartlepoolvTorquayLeague Two · England | 4–1 | League Two · England |
| 1998-10-20 | ChestervHartlepoolLeague Two · England | 1–1 | League Two · England |
| 1998-10-17 | BrentfordvHartlepoolLeague Two · England | 3–1 | League Two · England |
| 1998-10-10 | HartlepoolvShrewsburyLeague Two · England | 1–1 | League Two · England |
| 1998-10-03 | Leyton OrientvHartlepoolLeague Two · England | 1–1 | League Two · England |
| 1998-09-27 | HartlepoolvPeterboroLeague Two · England | 1–2 | League Two · England |
| 1998-09-19 | RotherhamvHartlepoolLeague Two · England | 3–0 | League Two · England |
| 1998-09-12 | HartlepoolvExeterLeague Two · England | 4–3 | League Two · England |
| 1998-09-08 | DarlingtonvHartlepoolLeague Two · England | 2–0 | League Two · England |
| 1998-09-04 | HalifaxvHartlepoolLeague Two · England | 2–1 | League Two · England |
| 1998-08-31 | HartlepoolvHullLeague Two · England | 1–0 | League Two · England |
| 1998-08-29 | CambridgevHartlepoolLeague Two · England | 1–2 | League Two · England |
| 1998-08-22 | HartlepoolvScunthorpeLeague Two · England | 1–2 | League Two · England |
| 1998-08-15 | BarnetvHartlepoolLeague Two · England | 0–2 | League Two · England |
| 1998-08-08 | HartlepoolvCardiffLeague Two · England | 1–1 | League Two · England |
| 1998-05-02 | PeterborovHartlepoolLeague Two · England | 0–0 | League Two · England |
| 1998-04-25 | HartlepoolvCardiffLeague Two · England | 2–0 | League Two · England |
| 1998-04-18 | MansfieldvHartlepoolLeague Two · England | 2–2 | League Two · England |
| 1998-04-13 | HartlepoolvLincolnLeague Two · England | 1–1 | League Two · England |
| 1998-04-11 | HullvHartlepoolLeague Two · England | 2–1 | League Two · England |
| 1998-04-04 | HartlepoolvCambridgeLeague Two · England | 3–3 | League Two · England |
| 1998-03-29 | BarnetvHartlepoolLeague Two · England | 1–1 | League Two · England |
| 1998-03-21 | RochdalevHartlepoolLeague Two · England | 2–1 | League Two · England |
| 1998-03-14 | HartlepoolvSwanseaLeague Two · England | 4–2 | League Two · England |
| 1998-03-07 | BrightonvHartlepoolLeague Two · England | 0–0 | League Two · England |
| 1998-03-03 | HartlepoolvScunthorpeLeague Two · England | 0–1 | League Two · England |
| 1998-02-28 | HartlepoolvDoncasterLeague Two · England | 3–1 | League Two · England |
| 1998-02-24 | Leyton OrientvHartlepoolLeague Two · England | 2–1 | League Two · England |
| 1998-02-21 | ShrewsburyvHartlepoolLeague Two · England | 1–0 | League Two · England |
| 1998-02-14 | HartlepoolvChesterLeague Two · England | 0–0 | League Two · England |
| 1998-02-07 | HartlepoolvDarlingtonLeague Two · England | 2–2 | League Two · England |
| 1998-01-31 | TorquayvHartlepoolLeague Two · England | 1–0 | League Two · England |
| 1998-01-24 | HartlepoolvRotherhamLeague Two · England | 0–0 | League Two · England |
| 1998-01-17 | MacclesfieldvHartlepoolLeague Two · England | 2–1 | League Two · England |
| 1998-01-10 | HartlepoolvExeterLeague Two · England | 1–1 | League Two · England |
| 1998-01-03 | ColchestervHartlepoolLeague Two · England | 1–2 | League Two · England |