| 2000-02-12 | MacclesfieldvBarnetLeague Two · England | 2–0 | League Two · England |
| 2000-02-05 | RotherhamvMacclesfieldLeague Two · England | 2–1 | League Two · England |
| 2000-01-29 | MacclesfieldvHullLeague Two · England | 0–2 | League Two · England |
| 2000-01-22 | SwanseavMacclesfieldLeague Two · England | 1–0 | League Two · England |
| 2000-01-15 | MacclesfieldvDarlingtonLeague Two · England | 2–1 | League Two · England |
| 2000-01-08 | MacclesfieldvCheltenhamLeague Two · England | 1–2 | League Two · England |
| 2000-01-03 | PlymouthvMacclesfieldLeague Two · England | 3–2 | League Two · England |
| 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 |
| 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 |