| 1999-05-08 | CambridgevBrentfordLeague Two · England | 0–1 | League Two · England |
| 1999-05-06 | SwanseavCambridgeLeague Two · England | 2–0 | League Two · England |
| 1999-05-01 | PlymouthvCambridgeLeague Two · England | 2–2 | League Two · England |
| 1999-04-27 | RochdalevCambridgeLeague Two · England | 0–2 | League Two · England |
| 1999-04-24 | CambridgevPeterboroLeague Two · England | 1–1 | League Two · England |
| 1999-04-17 | DarlingtonvCambridgeLeague Two · England | 0–0 | League Two · England |
| 1999-04-13 | CambridgevRochdaleLeague Two · England | 1–1 | League Two · England |
| 1999-04-10 | CambridgevHalifaxLeague Two · England | 4–0 | League Two · England |
| 1999-04-06 | BrightonvCambridgeLeague Two · England | 1–3 | League Two · England |
| 1999-04-03 | CambridgevCardiffLeague Two · England | 0–0 | League Two · England |
| 1999-03-26 | ShrewsburyvCambridgeLeague Two · England | 1–1 | League Two · England |
| 1999-03-20 | CambridgevMansfieldLeague Two · England | 7–2 | League Two · England |
| 1999-03-13 | BarnetvCambridgeLeague Two · England | 3–0 | League Two · England |
| 1999-03-09 | CambridgevHullLeague Two · England | 2–0 | League Two · England |
| 1999-03-06 | ExetervCambridgeLeague Two · England | 0–3 | League Two · England |
| 1999-02-27 | CambridgevSouthendLeague Two · England | 3–0 | League Two · England |
| 1999-02-20 | Leyton OrientvCambridgeLeague Two · England | 2–0 | League Two · England |
| 1999-02-13 | CambridgevScunthorpeLeague Two · England | 0–0 | League Two · England |
| 1999-02-06 | ScarboroughvCambridgeLeague Two · England | 1–5 | League Two · England |
| 1999-01-30 | CambridgevCarlisleLeague Two · England | 1–0 | League Two · England |
| 1999-01-23 | CambridgevChesterLeague Two · England | 2–1 | League Two · England |
| 1999-01-09 | CambridgevTorquayLeague Two · England | 2–0 | League Two · England |
| 1999-01-02 | HartlepoolvCambridgeLeague Two · England | 2–2 | League Two · England |