| 1999-12-28 | LincolnvHartlepoolLeague Two · England | 1–2 | League Two · England |
| 1999-12-26 | HalifaxvLincolnLeague Two · England | 3–0 | League Two · England |
| 1999-12-18 | LincolnvShrewsburyLeague Two · England | 1–2 | League Two · England |
| 1999-12-04 | RotherhamvLincolnLeague Two · England | 1–1 | League Two · England |
| 1999-11-27 | LincolnvRochdaleLeague Two · England | 1–1 | League Two · England |
| 1999-11-23 | BrightonvLincolnLeague Two · England | 2–2 | League Two · England |
| 1999-11-12 | LincolnvYorkLeague Two · England | 4–2 | League Two · England |
| 1999-11-06 | MansfieldvLincolnLeague Two · England | 5–2 | League Two · England |
| 1999-11-02 | LincolnvPeterboroLeague Two · England | 1–2 | League Two · England |
| 1999-10-23 | LincolnvChesterLeague Two · England | 4–1 | League Two · England |
| 1999-10-19 | SouthendvLincolnLeague Two · England | 2–2 | League Two · England |
| 1999-10-16 | Leyton OrientvLincolnLeague Two · England | 2–3 | League Two · England |
| 1999-10-09 | LincolnvDarlingtonLeague Two · England | 1–0 | League Two · England |
| 1999-10-02 | LincolnvExeterLeague Two · England | 1–0 | League Two · England |
| 1999-09-25 | ChestervLincolnLeague Two · England | 1–3 | League Two · England |
| 1999-09-18 | LincolnvMacclesfieldLeague Two · England | 1–1 | League Two · England |
| 1999-09-11 | CarlislevLincolnLeague Two · England | 1–0 | League Two · England |
| 1999-09-04 | TorquayvLincolnLeague Two · England | 5–2 | League Two · England |
| 1999-08-30 | LincolnvSwanseaLeague Two · England | 0–1 | League Two · England |
| 1999-08-27 | NorthamptonvLincolnLeague Two · England | 1–0 | League Two · England |
| 1999-08-21 | LincolnvBarnetLeague Two · England | 0–0 | League Two · England |
| 1999-08-14 | HullvLincolnLeague Two · England | 1–1 | League Two · England |
| 1999-08-07 | LincolnvRotherhamLeague Two · England | 2–1 | League Two · England |