| 1999-12-28 | RochdalevShrewsburyLeague Two · England | 2–1 | League Two · England |
| 1999-12-26 | ShrewsburyvMacclesfieldLeague Two · England | 0–1 | League Two · England |
| 1999-12-18 | LincolnvShrewsburyLeague Two · England | 1–2 | League Two · England |
| 1999-12-11 | ShrewsburyvNorthamptonLeague Two · England | 1–0 | League Two · England |
| 1999-12-04 | TorquayvShrewsburyLeague Two · England | 3–1 | League Two · England |
| 1999-11-27 | ShrewsburyvHullLeague Two · England | 3–0 | League Two · England |
| 1999-11-23 | YorkvShrewsburyLeague Two · England | 1–0 | League Two · England |
| 1999-11-12 | ShrewsburyvSwanseaLeague Two · England | 1–1 | League Two · England |
| 1999-11-06 | PeterborovShrewsburyLeague Two · England | 4–1 | League Two · England |
| 1999-11-02 | ShrewsburyvChesterLeague Two · England | 0–1 | League Two · England |
| 1999-10-23 | ShrewsburyvMansfieldLeague Two · England | 1–2 | League Two · England |
| 1999-10-19 | BrightonvShrewsburyLeague Two · England | 1–0 | League Two · England |
| 1999-10-16 | SouthendvShrewsburyLeague Two · England | 3–2 | League Two · England |
| 1999-10-09 | ShrewsburyvExeterLeague Two · England | 1–4 | League Two · England |
| 1999-10-02 | ShrewsburyvHalifaxLeague Two · England | 0–0 | League Two · England |
| 1999-09-24 | MansfieldvShrewsburyLeague Two · England | 4–0 | League Two · England |
| 1999-09-18 | ShrewsburyvCarlisleLeague Two · England | 4–1 | League Two · England |
| 1999-09-12 | CheltenhamvShrewsburyLeague Two · England | 0–1 | League Two · England |
| 1999-09-03 | Leyton OrientvShrewsburyLeague Two · England | 1–2 | League Two · England |
| 1999-08-31 | ShrewsburyvHartlepoolLeague Two · England | 0–0 | League Two · England |
| 1999-08-28 | RotherhamvShrewsburyLeague Two · England | 4–0 | League Two · England |
| 1999-08-21 | ShrewsburyvDarlingtonLeague Two · England | 0–1 | League Two · England |
| 1999-08-14 | PlymouthvShrewsburyLeague Two · England | 0–0 | League Two · England |
| 1999-08-07 | ShrewsburyvTorquayLeague Two · England | 1–2 | League Two · England |
| 1999-05-08 | TorquayvShrewsburyLeague Two · England | 0–3 | League Two · England |
| 1999-05-01 | ShrewsburyvMansfieldLeague Two · England | 1–0 | League Two · England |
| 1999-04-24 | Leyton OrientvShrewsburyLeague Two · England | 6–1 | League Two · England |
| 1999-04-20 | ShrewsburyvRotherhamLeague Two · England | 2–3 | League Two · England |
| 1999-04-17 | ShrewsburyvExeterLeague Two · England | 1–1 | League Two · England |
| 1999-04-13 | BrightonvShrewsburyLeague Two · England | 1–0 | League Two · England |
| 1999-04-09 | SwanseavShrewsburyLeague Two · England | 1–1 | League Two · England |
| 1999-04-06 | ShrewsburyvHartlepoolLeague Two · England | 0–1 | League Two · England |
| 1999-04-03 | PlymouthvShrewsburyLeague Two · England | 2–0 | League Two · England |
| 1999-03-26 | ShrewsburyvCambridgeLeague Two · England | 1–1 | League Two · England |
| 1999-03-20 | ShrewsburyvChesterLeague Two · England | 2–0 | League Two · England |
| 1999-03-13 | BrentfordvShrewsburyLeague Two · England | 0–0 | League Two · England |
| 1999-03-06 | CarlislevShrewsburyLeague Two · England | 2–1 | League Two · England |
| 1999-02-27 | ShrewsburyvDarlingtonLeague Two · England | 3–0 | League Two · England |
| 1999-02-20 | PeterborovShrewsburyLeague Two · England | 2–2 | League Two · England |
| 1999-02-13 | ShrewsburyvScarboroughLeague Two · England | 3–1 | League Two · England |
| 1999-02-06 | ShrewsburyvRochdaleLeague Two · England | 3–2 | League Two · England |
| 1999-01-30 | HullvShrewsburyLeague Two · England | 1–1 | League Two · England |
| 1999-01-23 | BarnetvShrewsburyLeague Two · England | 2–2 | League Two · England |
| 1999-01-16 | ShrewsburyvSouthendLeague Two · England | 3–1 | League Two · England |
| 1999-01-09 | ScunthorpevShrewsburyLeague Two · England | 3–0 | League Two · England |
| 1999-01-02 | ShrewsburyvHalifaxLeague Two · England | 2–2 | League Two · England |