| 1999-12-28 | CambridgevCardiffLeague One · England | 0–0 | League One · England |
| 1999-12-26 | CardiffvReadingLeague One · England | 1–0 | League One · England |
| 1999-12-18 | BurnleyvCardiffLeague One · England | 2–1 | League One · England |
| 1999-12-04 | MillwallvCardiffLeague One · England | 2–0 | League One · England |
| 1999-11-27 | CardiffvGillinghamLeague One · England | 1–2 | League One · England |
| 1999-11-23 | ColchestervCardiffLeague One · England | 0–3 | League One · England |
| 1999-11-12 | CardiffvChesterfieldLeague One · England | 2–1 | League One · England |
| 1999-11-06 | BournemouthvCardiffLeague One · England | 1–0 | League One · England |
| 1999-11-02 | CardiffvBlackpoolLeague One · England | 1–1 | League One · England |
| 1999-10-23 | WiganvCardiffLeague One · England | 2–0 | League One · England |
| 1999-10-19 | CardiffvStokeLeague One · England | 1–2 | League One · England |
| 1999-10-16 | CardiffvOldhamLeague One · England | 1–1 | League One · England |
| 1999-10-09 | Bristol RvsvCardiffLeague One · England | 1–1 | League One · England |
| 1999-10-02 | BuryvCardiffLeague One · England | 3–2 | League One · England |
| 1999-09-28 | BrentfordvCardiffLeague One · England | 2–1 | League One · England |
| 1999-09-25 | CardiffvWiganLeague One · England | 0–0 | League One · England |
| 1999-09-18 | CardiffvNotts CountyLeague One · England | 2–1 | League One · England |
| 1999-09-11 | WycombevCardiffLeague One · England | 3–1 | League One · England |
| 1999-08-30 | CardiffvScunthorpeLeague One · England | 1–1 | League One · England |
| 1999-08-28 | LutonvCardiffLeague One · England | 1–0 | League One · England |
| 1999-08-22 | CardiffvWrexhamLeague One · England | 1–1 | League One · England |
| 1999-08-14 | OxfordvCardiffLeague One · England | 2–3 | League One · England |
| 1999-08-07 | CardiffvMillwallLeague One · England | 1–1 | League One · England |