| 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 |
| 1998-12-28 | MacclesfieldvBlackpoolLeague One · England | 0–1 | League One · England |
| 1998-12-26 | LincolnvMacclesfieldLeague One · England | 1–0 | League One · England |
| 1998-12-18 | Bristol RvsvMacclesfieldLeague One · England | 0–0 | League One · England |
| 1998-12-12 | MacclesfieldvLutonLeague One · England | 2–2 | League One · England |
| 1998-11-28 | ChesterfieldvMacclesfieldLeague One · England | 2–0 | League One · England |
| 1998-11-21 | MacclesfieldvWalsallLeague One · England | 1–1 | League One · England |
| 1998-11-10 | YorkvMacclesfieldLeague One · England | 0–2 | League One · England |
| 1998-11-06 | ColchestervMacclesfieldLeague One · England | 1–1 | League One · England |
| 1998-10-31 | MacclesfieldvNorthamptonLeague One · England | 0–1 | League One · England |
| 1998-10-24 | MacclesfieldvBurnleyLeague One · England | 2–1 | League One · England |
| 1998-10-20 | PrestonvMacclesfieldLeague One · England | 2–2 | League One · England |
| 1998-10-17 | WycombevMacclesfieldLeague One · England | 3–0 | League One · England |
| 1998-10-10 | MacclesfieldvBournemouthLeague One · England | 2–2 | League One · England |
| 1998-10-03 | GillinghamvMacclesfieldLeague One · England | 2–2 | League One · England |
| 1998-09-27 | MacclesfieldvReadingLeague One · England | 2–1 | League One · England |
| 1998-09-19 | WiganvMacclesfieldLeague One · England | 2–0 | League One · England |
| 1998-09-12 | MacclesfieldvMan CityLeague One · England | 0–1 | League One · England |
| 1998-09-08 | OldhamvMacclesfieldLeague One · England | 1–2 | League One · England |
| 1998-09-05 | WrexhamvMacclesfieldLeague One · England | 2–1 | League One · England |
| 1998-08-31 | MacclesfieldvNotts CountyLeague One · England | 0–1 | League One · England |
| 1998-08-29 | MillwallvMacclesfieldLeague One · England | 0–0 | League One · England |
| 1998-08-22 | MacclesfieldvLincolnLeague One · England | 0–0 | League One · England |
| 1998-08-15 | StokevMacclesfieldLeague One · England | 2–0 | League One · England |
| 1998-08-08 | MacclesfieldvFulhamLeague One · England | 0–1 | League One · England |