| 1999-12-28 | CambridgevCardiffLeague One · England | 0–0 | League One · England |
| 1999-12-26 | OxfordvCambridgeLeague One · England | 1–0 | League One · England |
| 1999-12-18 | CambridgevOldhamLeague One · England | 2–3 | League One · England |
| 1999-12-04 | CambridgevBournemouthLeague One · England | 0–2 | League One · England |
| 1999-11-27 | BlackpoolvCambridgeLeague One · England | 2–1 | League One · England |
| 1999-11-23 | WrexhamvCambridgeLeague One · England | 1–1 | League One · England |
| 1999-11-12 | CambridgevLutonLeague One · England | 3–1 | League One · England |
| 1999-11-06 | Bristol CityvCambridgeLeague One · England | 1–1 | League One · England |
| 1999-11-02 | CambridgevScunthorpeLeague One · England | 1–3 | League One · England |
| 1999-10-23 | GillinghamvCambridgeLeague One · England | 2–1 | League One · England |
| 1999-10-19 | CambridgevBurnleyLeague One · England | 0–1 | League One · England |
| 1999-10-15 | CambridgevColchesterLeague One · England | 5–2 | League One · England |
| 1999-10-09 | WycombevCambridgeLeague One · England | 1–0 | League One · England |
| 1999-10-02 | PrestonvCambridgeLeague One · England | 2–1 | League One · England |
| 1999-09-25 | CambridgevGillinghamLeague One · England | 2–2 | League One · England |
| 1999-09-18 | MillwallvCambridgeLeague One · England | 2–1 | League One · England |
| 1999-09-11 | CambridgevBrentfordLeague One · England | 2–2 | League One · England |
| 1999-09-04 | CambridgevStokeLeague One · England | 1–3 | League One · England |
| 1999-08-30 | WiganvCambridgeLeague One · England | 1–1 | League One · England |
| 1999-08-28 | CambridgevNotts CountyLeague One · England | 1–1 | League One · England |
| 1999-08-21 | ChesterfieldvCambridgeLeague One · England | 4–2 | League One · England |
| 1999-08-14 | CambridgevReadingLeague One · England | 3–1 | League One · England |
| 1999-08-07 | BournemouthvCambridgeLeague One · England | 2–1 | League One · England |
| 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 |