| 1999-12-28 | SwanseavPlymouthLeague Two · England | 1–0 | League Two · England |
| 1999-12-26 | Leyton OrientvSwanseaLeague Two · England | 0–1 | League Two · England |
| 1999-12-18 | SwanseavBrightonLeague Two · England | 2–0 | League Two · England |
| 1999-12-11 | HartlepoolvSwanseaLeague Two · England | 0–1 | League Two · England |
| 1999-12-04 | SwanseavYorkLeague Two · England | 1–0 | League Two · England |
| 1999-11-27 | ChestervSwanseaLeague Two · England | 0–1 | League Two · England |
| 1999-11-23 | SwanseavDarlingtonLeague Two · England | 0–0 | League Two · England |
| 1999-11-16 | SwanseavCheltenhamLeague Two · England | 0–0 | League Two · England |
| 1999-11-12 | ShrewsburyvSwanseaLeague Two · England | 1–1 | League Two · England |
| 1999-11-05 | SwanseavHalifaxLeague Two · England | 3–1 | League Two · England |
| 1999-11-02 | NorthamptonvSwanseaLeague Two · England | 2–1 | League Two · England |
| 1999-10-22 | SwanseavRochdaleLeague Two · England | 1–0 | League Two · England |
| 1999-10-19 | ExetervSwanseaLeague Two · England | 1–1 | League Two · England |
| 1999-10-16 | TorquayvSwanseaLeague Two · England | 1–0 | League Two · England |
| 1999-10-12 | SwanseavRotherhamLeague Two · England | 2–0 | League Two · England |
| 1999-10-02 | SwanseavMansfieldLeague Two · England | 0–1 | League Two · England |
| 1999-09-25 | RochdalevSwanseaLeague Two · England | 0–0 | League Two · England |
| 1999-09-18 | HullvSwanseaLeague Two · England | 2–0 | League Two · England |
| 1999-09-11 | SwanseavBarnetLeague Two · England | 1–2 | League Two · England |
| 1999-08-30 | LincolnvSwanseaLeague Two · England | 0–1 | League Two · England |
| 1999-08-28 | SwanseavSouthendLeague Two · England | 3–1 | League Two · England |
| 1999-08-21 | MacclesfieldvSwanseaLeague Two · England | 1–2 | League Two · England |
| 1999-08-14 | SwanseavCarlisleLeague Two · England | 1–0 | League Two · England |
| 1999-08-07 | YorkvSwanseaLeague Two · England | 1–0 | League Two · England |
| 1999-05-08 | SwanseavHullLeague Two · England | 2–0 | League Two · England |
| 1999-05-06 | SwanseavCambridgeLeague Two · England | 2–0 | League Two · England |
| 1999-05-04 | BrentfordvSwanseaLeague Two · England | 4–1 | League Two · England |
| 1999-05-01 | RochdalevSwanseaLeague Two · England | 0–3 | League Two · England |
| 1999-04-24 | SwanseavPlymouthLeague Two · England | 2–3 | League Two · England |
| 1999-04-18 | CardiffvSwanseaLeague Two · England | 0–0 | League Two · England |
| 1999-04-13 | SwanseavHartlepoolLeague Two · England | 1–0 | League Two · England |
| 1999-04-09 | SwanseavShrewsburyLeague Two · England | 1–1 | League Two · England |
| 1999-04-05 | RotherhamvSwanseaLeague Two · England | 1–0 | League Two · England |
| 1999-04-03 | SwanseavChesterLeague Two · England | 1–1 | League Two · England |
| 1999-03-23 | ScunthorpevSwanseaLeague Two · England | 1–2 | League Two · England |
| 1999-03-20 | SwanseavHalifaxLeague Two · England | 1–2 | League Two · England |
| 1999-03-13 | PeterborovSwanseaLeague Two · England | 0–1 | League Two · England |
| 1999-03-09 | SwanseavDarlingtonLeague Two · England | 2–0 | League Two · England |
| 1999-03-06 | SouthendvSwanseaLeague Two · England | 2–0 | League Two · England |
| 1999-02-27 | SwanseavTorquayLeague Two · England | 0–0 | League Two · England |
| 1999-02-23 | SwanseavMansfieldLeague Two · England | 1–0 | League Two · England |
| 1999-02-20 | ScarboroughvSwanseaLeague Two · England | 2–1 | League Two · England |
| 1999-02-16 | SwanseavBrentfordLeague Two · England | 2–1 | League Two · England |
| 1999-02-13 | SwanseavCarlisleLeague Two · England | 1–1 | League Two · England |
| 1999-02-05 | SwanseavBrightonLeague Two · England | 2–2 | League Two · England |
| 1999-01-30 | BarnetvSwanseaLeague Two · England | 0–1 | League Two · England |
| 1999-01-09 | ExetervSwanseaLeague Two · England | 4–0 | League Two · England |