| 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 |
| 1998-05-02 | ExetervMacclesfieldLeague Two · England | 1–3 | League Two · England |
| 1998-04-25 | MacclesfieldvChesterLeague Two · England | 3–2 | League Two · England |
| 1998-04-18 | CardiffvMacclesfieldLeague Two · England | 1–2 | League Two · England |
| 1998-04-13 | MacclesfieldvBarnetLeague Two · England | 2–0 | League Two · England |
| 1998-04-11 | ScunthorpevMacclesfieldLeague Two · England | 1–0 | League Two · England |
| 1998-04-04 | MacclesfieldvLincolnLeague Two · England | 1–0 | League Two · England |
| 1998-03-29 | HullvMacclesfieldLeague Two · England | 0–0 | League Two · England |
| 1998-03-21 | MacclesfieldvShrewsburyLeague Two · England | 2–1 | League Two · England |
| 1998-03-14 | ColchestervMacclesfieldLeague Two · England | 5–1 | League Two · England |
| 1998-03-07 | MacclesfieldvRotherhamLeague Two · England | 0–0 | League Two · England |
| 1998-03-03 | CambridgevMacclesfieldLeague Two · England | 0–0 | League Two · England |
| 1998-02-28 | MacclesfieldvNotts CountyLeague Two · England | 2–0 | League Two · England |
| 1998-02-24 | MansfieldvMacclesfieldLeague Two · England | 1–0 | League Two · England |
| 1998-02-21 | PeterborovMacclesfieldLeague Two · England | 0–1 | League Two · England |
| 1998-02-14 | MacclesfieldvLeyton OrientLeague Two · England | 1–0 | League Two · England |
| 1998-02-07 | MacclesfieldvScarboroughLeague Two · England | 3–1 | League Two · England |
| 1998-01-31 | SwanseavMacclesfieldLeague Two · England | 1–1 | League Two · England |
| 1998-01-27 | MacclesfieldvBrightonLeague Two · England | 1–0 | League Two · England |
| 1998-01-24 | DoncastervMacclesfieldLeague Two · England | 0–3 | League Two · England |
| 1998-01-20 | MacclesfieldvScunthorpeLeague Two · England | 2–0 | League Two · England |
| 1998-01-17 | MacclesfieldvHartlepoolLeague Two · England | 2–1 | League Two · England |
| 1998-01-10 | TorquayvMacclesfieldLeague Two · England | 2–0 | League Two · England |