| 1999-12-28 | MacclesfieldvCarlisleLeague Two · England | 2–1 | League Two · England |
| 1999-12-26 | ShrewsburyvMacclesfieldLeague Two · England | 0–1 | League Two · England |
| 1999-12-18 | MacclesfieldvLeyton OrientLeague Two · England | 1–0 | League Two · England |
| 1999-12-11 | CheltenhamvMacclesfieldLeague Two · England | 1–1 | League Two · England |
| 1999-12-04 | NorthamptonvMacclesfieldLeague Two · England | 2–0 | League Two · England |
| 1999-11-27 | MacclesfieldvHartlepoolLeague Two · England | 3–3 | League Two · England |
| 1999-11-20 | PeterborovMacclesfieldLeague Two · England | 2–2 | League Two · England |
| 1999-11-14 | MacclesfieldvBrightonLeague Two · England | 1–1 | League Two · England |
| 1999-11-06 | YorkvMacclesfieldLeague Two · England | 0–2 | League Two · England |
| 1999-11-02 | MacclesfieldvMansfieldLeague Two · England | 5–2 | League Two · England |
| 1999-10-23 | MacclesfieldvExeterLeague Two · England | 1–0 | League Two · England |
| 1999-10-19 | RochdalevMacclesfieldLeague Two · England | 0–1 | League Two · England |
| 1999-10-16 | ChestervMacclesfieldLeague Two · England | 1–2 | League Two · England |
| 1999-10-09 | MacclesfieldvHalifaxLeague Two · England | 0–2 | League Two · England |
| 1999-10-02 | MacclesfieldvTorquayLeague Two · England | 1–2 | League Two · England |
| 1999-09-25 | ExetervMacclesfieldLeague Two · England | 0–3 | League Two · England |
| 1999-09-18 | LincolnvMacclesfieldLeague Two · England | 1–1 | League Two · England |
| 1999-09-11 | MacclesfieldvSouthendLeague Two · England | 1–2 | League Two · England |
| 1999-09-05 | BarnetvMacclesfieldLeague Two · England | 2–1 | League Two · England |
| 1999-08-30 | MacclesfieldvRotherhamLeague Two · England | 1–1 | League Two · England |
| 1999-08-28 | HullvMacclesfieldLeague Two · England | 2–3 | League Two · England |
| 1999-08-21 | MacclesfieldvSwanseaLeague Two · England | 1–2 | League Two · England |
| 1999-08-14 | DarlingtonvMacclesfieldLeague Two · England | 3–0 | League Two · England |
| 1999-08-07 | MacclesfieldvNorthamptonLeague Two · England | 1–0 | League Two · England |
| 1999-05-08 | MacclesfieldvBristol RvsLeague One · England | 3–4 | League One · England |
| 1999-05-04 | Notts CountyvMacclesfieldLeague One · England | 1–1 | League One · England |
| 1999-05-01 | LutonvMacclesfieldLeague One · England | 1–2 | League One · England |
| 1999-04-27 | MacclesfieldvStokeLeague One · England | 1–2 | League One · England |
| 1999-04-24 | MacclesfieldvYorkLeague One · England | 1–2 | League One · England |
| 1999-04-17 | WalsallvMacclesfieldLeague One · England | 2–0 | League One · England |
| 1999-04-13 | MacclesfieldvChesterfieldLeague One · England | 2–0 | League One · England |
| 1999-04-10 | MacclesfieldvPrestonLeague One · England | 3–2 | League One · England |
| 1999-04-06 | BournemouthvMacclesfieldLeague One · England | 1–0 | League One · England |
| 1999-04-03 | MacclesfieldvWycombeLeague One · England | 1–3 | League One · England |
| 1999-03-28 | BurnleyvMacclesfieldLeague One · England | 4–3 | League One · England |
| 1999-03-20 | NorthamptonvMacclesfieldLeague One · England | 0–2 | League One · England |
| 1999-03-13 | MacclesfieldvColchesterLeague One · England | 2–0 | League One · England |
| 1999-03-09 | MacclesfieldvGillinghamLeague One · England | 1–0 | League One · England |
| 1999-03-06 | ReadingvMacclesfieldLeague One · England | 1–0 | League One · England |
| 1999-02-27 | MacclesfieldvWiganLeague One · England | 0–1 | League One · England |
| 1999-02-20 | Man CityvMacclesfieldLeague One · England | 2–0 | League One · England |
| 1999-02-13 | MacclesfieldvOldhamLeague One · England | 1–0 | League One · England |
| 1999-02-06 | MacclesfieldvWrexhamLeague One · England | 0–2 | League One · England |
| 1999-01-30 | BlackpoolvMacclesfieldLeague One · England | 2–1 | League One · England |
| 1999-01-26 | MacclesfieldvMillwallLeague One · England | 0–2 | League One · England |
| 1999-01-09 | FulhamvMacclesfieldLeague One · England | 1–0 | League One · England |