| 1999-12-28 | HullvMansfieldLeague Two · England | 2–0 | League Two · England |
| 1999-12-26 | MansfieldvChesterLeague Two · England | 2–1 | League Two · England |
| 1999-12-18 | BarnetvMansfieldLeague Two · England | 0–0 | League Two · England |
| 1999-11-27 | HalifaxvMansfieldLeague Two · England | 0–1 | League Two · England |
| 1999-11-23 | MansfieldvRotherhamLeague Two · England | 1–2 | League Two · England |
| 1999-11-14 | RochdalevMansfieldLeague Two · England | 2–1 | League Two · England |
| 1999-11-06 | MansfieldvLincolnLeague Two · England | 5–2 | League Two · England |
| 1999-11-02 | MacclesfieldvMansfieldLeague Two · England | 5–2 | League Two · England |
| 1999-10-23 | ShrewsburyvMansfieldLeague Two · England | 1–2 | League Two · England |
| 1999-10-19 | MansfieldvNorthamptonLeague Two · England | 0–0 | League Two · England |
| 1999-10-16 | MansfieldvHartlepoolLeague Two · England | 2–3 | League Two · England |
| 1999-10-09 | PlymouthvMansfieldLeague Two · England | 2–1 | League Two · England |
| 1999-10-02 | SwanseavMansfieldLeague Two · England | 0–1 | League Two · England |
| 1999-09-24 | MansfieldvShrewsburyLeague Two · England | 4–0 | League Two · England |
| 1999-09-18 | DarlingtonvMansfieldLeague Two · England | 0–0 | League Two · England |
| 1999-09-11 | MansfieldvLeyton OrientLeague Two · England | 1–1 | League Two · England |
| 1999-09-03 | MansfieldvPeterboroLeague Two · England | 3–1 | League Two · England |
| 1999-08-30 | ExetervMansfieldLeague Two · England | 1–0 | League Two · England |
| 1999-08-28 | MansfieldvCarlisleLeague Two · England | 1–1 | League Two · England |
| 1999-08-21 | SouthendvMansfieldLeague Two · England | 1–0 | League Two · England |
| 1999-08-14 | MansfieldvCheltenhamLeague Two · England | 0–1 | League Two · England |
| 1999-08-07 | BrightonvMansfieldLeague Two · England | 6–0 | League Two · England |
| 1999-05-08 | MansfieldvCardiffLeague Two · England | 3–0 | League Two · England |
| 1999-05-01 | ShrewsburyvMansfieldLeague Two · England | 1–0 | League Two · England |
| 1999-04-27 | MansfieldvExeterLeague Two · England | 0–1 | League Two · England |
| 1999-04-24 | MansfieldvHartlepoolLeague Two · England | 2–0 | League Two · England |
| 1999-04-17 | BarnetvMansfieldLeague Two · England | 0–0 | League Two · England |
| 1999-04-13 | MansfieldvHalifaxLeague Two · England | 0–1 | League Two · England |
| 1999-04-10 | MansfieldvSouthendLeague Two · England | 0–0 | League Two · England |
| 1999-04-05 | TorquayvMansfieldLeague Two · England | 0–0 | League Two · England |
| 1999-04-03 | MansfieldvBrightonLeague Two · England | 2–0 | League Two · England |
| 1999-03-28 | PeterborovMansfieldLeague Two · England | 1–0 | League Two · England |
| 1999-03-20 | CambridgevMansfieldLeague Two · England | 7–2 | League Two · England |
| 1999-03-13 | MansfieldvRochdaleLeague Two · England | 3–1 | League Two · England |
| 1999-03-06 | HullvMansfieldLeague Two · England | 0–0 | League Two · England |
| 1999-02-27 | MansfieldvScunthorpeLeague Two · England | 2–1 | League Two · England |
| 1999-02-23 | SwanseavMansfieldLeague Two · England | 1–0 | League Two · England |
| 1999-02-20 | CarlislevMansfieldLeague Two · England | 0–0 | League Two · England |
| 1999-02-13 | MansfieldvLeyton OrientLeague Two · England | 1–2 | League Two · England |
| 1999-02-06 | DarlingtonvMansfieldLeague Two · England | 5–1 | League Two · England |
| 1999-01-30 | MansfieldvChesterLeague Two · England | 3–0 | League Two · England |
| 1999-01-22 | MansfieldvRotherhamLeague Two · England | 0–3 | League Two · England |
| 1999-01-16 | PlymouthvMansfieldLeague Two · England | 3–0 | League Two · England |
| 1999-01-09 | MansfieldvBrentfordLeague Two · England | 3–1 | League Two · England |