| 1999-05-08 | NorthamptonvBurnleyLeague One · England | 2–2 | League One · England |
| 1999-05-03 | ChesterfieldvNorthamptonLeague One · England | 0–0 | League One · England |
| 1999-04-29 | NorthamptonvWiganLeague One · England | 3–3 | League One · England |
| 1999-04-24 | NorthamptonvColchesterLeague One · England | 3–3 | League One · England |
| 1999-04-17 | ReadingvNorthamptonLeague One · England | 0–1 | League One · England |
| 1999-04-13 | NorthamptonvYorkLeague One · England | 2–2 | League One · England |
| 1999-04-10 | NorthamptonvLutonLeague One · England | 1–0 | League One · England |
| 1999-04-05 | Bristol RvsvNorthamptonLeague One · England | 1–1 | League One · England |
| 1999-04-02 | NorthamptonvBournemouthLeague One · England | 2–1 | League One · England |
| 1999-03-27 | PrestonvNorthamptonLeague One · England | 3–0 | League One · England |
| 1999-03-20 | NorthamptonvMacclesfieldLeague One · England | 0–2 | League One · England |
| 1999-03-13 | WycombevNorthamptonLeague One · England | 1–2 | League One · England |
| 1999-03-06 | Man CityvNorthamptonLeague One · England | 0–0 | League One · England |
| 1999-03-02 | NorthamptonvWrexhamLeague One · England | 0–2 | League One · England |
| 1999-02-27 | NorthamptonvMillwallLeague One · England | 1–2 | League One · England |
| 1999-02-23 | NorthamptonvWalsallLeague One · England | 0–1 | League One · England |
| 1999-02-20 | OldhamvNorthamptonLeague One · England | 0–1 | League One · England |
| 1999-02-13 | NorthamptonvGillinghamLeague One · England | 0–1 | League One · England |
| 1999-02-06 | NorthamptonvBlackpoolLeague One · England | 0–0 | League One · England |
| 1999-01-30 | FulhamvNorthamptonLeague One · England | 2–0 | League One · England |
| 1999-01-23 | LincolnvNorthamptonLeague One · England | 1–0 | League One · England |
| 1999-01-09 | StokevNorthamptonLeague One · England | 3–1 | League One · England |