| 1999-05-08 | MansfieldvCardiffLeague Two · England | 3–0 | League Two · England |
| 1999-05-01 | CardiffvScunthorpeLeague Two · England | 0–0 | League Two · England |
| 1999-04-24 | ScarboroughvCardiffLeague Two · England | 1–2 | League Two · England |
| 1999-04-18 | CardiffvSwanseaLeague Two · England | 0–0 | League Two · England |
| 1999-04-13 | SouthendvCardiffLeague Two · England | 0–1 | League Two · England |
| 1999-04-10 | Leyton OrientvCardiffLeague Two · England | 1–1 | League Two · England |
| 1999-04-05 | CardiffvHullLeague Two · England | 1–1 | League Two · England |
| 1999-04-03 | CambridgevCardiffLeague Two · England | 0–0 | League Two · England |
| 1999-03-27 | CardiffvCarlisleLeague Two · England | 2–1 | League Two · England |
| 1999-03-20 | ExetervCardiffLeague Two · England | 0–2 | League Two · England |
| 1999-03-16 | RotherhamvCardiffLeague Two · England | 1–0 | League Two · England |
| 1999-03-13 | CardiffvTorquayLeague Two · England | 2–2 | League Two · England |
| 1999-03-09 | BrightonvCardiffLeague Two · England | 0–2 | League Two · England |
| 1999-03-05 | CardiffvChesterLeague Two · England | 0–0 | League Two · England |
| 1999-02-27 | RochdalevCardiffLeague Two · England | 1–1 | League Two · England |
| 1999-02-19 | CardiffvHalifaxLeague Two · England | 1–1 | League Two · England |
| 1999-02-13 | BarnetvCardiffLeague Two · England | 1–0 | League Two · England |
| 1999-02-06 | PlymouthvCardiffLeague Two · England | 1–1 | League Two · England |
| 1999-01-30 | CardiffvBrentfordLeague Two · England | 4–1 | League Two · England |
| 1999-01-23 | CardiffvDarlingtonLeague Two · England | 3–2 | League Two · England |
| 1999-01-16 | PeterborovCardiffLeague Two · England | 2–1 | League Two · England |
| 1999-01-09 | CardiffvHartlepoolLeague Two · England | 4–1 | League Two · England |