| 1999-12-28 | BarnsleyvPort ValeChampionship · England | 3–1 | Championship · England |
| 1999-12-26 | GrimsbyvBarnsleyChampionship · England | 0–3 | Championship · England |
| 1999-12-18 | BarnsleyvWalsallChampionship · England | 3–2 | Championship · England |
| 1999-12-04 | BarnsleyvCharltonChampionship · England | 1–1 | Championship · England |
| 1999-11-27 | QPRvBarnsleyChampionship · England | 2–2 | Championship · England |
| 1999-11-24 | Man CityvBarnsleyChampionship · England | 3–1 | Championship · England |
| 1999-11-20 | BarnsleyvBirminghamChampionship · England | 2–1 | Championship · England |
| 1999-11-13 | FulhamvBarnsleyChampionship · England | 1–3 | Championship · England |
| 1999-11-06 | BarnsleyvSheffield UnitedChampionship · England | 2–0 | Championship · England |
| 1999-10-30 | BarnsleyvNott'm ForestChampionship · England | 1–0 | Championship · England |
| 1999-10-26 | HuddersfieldvBarnsleyChampionship · England | 2–1 | Championship · England |
| 1999-10-23 | CrewevBarnsleyChampionship · England | 0–1 | Championship · England |
| 1999-10-19 | BarnsleyvSwindonChampionship · England | 1–0 | Championship · England |
| 1999-10-16 | BarnsleyvWolvesChampionship · England | 1–2 | Championship · England |
| 1999-10-01 | Nott'm ForestvBarnsleyChampionship · England | 3–0 | Championship · England |
| 1999-09-25 | BarnsleyvHuddersfieldChampionship · England | 4–2 | Championship · England |
| 1999-09-18 | BoltonvBarnsleyChampionship · England | 2–2 | Championship · England |
| 1999-09-10 | BarnsleyvStockportChampionship · England | 2–1 | Championship · England |
| 1999-09-03 | BarnsleyvTranmereChampionship · England | 3–0 | Championship · England |
| 1999-08-30 | IpswichvBarnsleyChampionship · England | 6–1 | Championship · England |
| 1999-08-28 | BarnsleyvPortsmouthChampionship · England | 6–0 | Championship · England |
| 1999-08-21 | BlackburnvBarnsleyChampionship · England | 1–2 | Championship · England |
| 1999-08-14 | BarnsleyvCrystal PalaceChampionship · England | 2–3 | Championship · England |
| 1999-08-07 | CharltonvBarnsleyChampionship · England | 3–1 | Championship · England |
| 1999-05-09 | SwindonvBarnsleyChampionship · England | 1–3 | Championship · England |
| 1999-05-01 | BarnsleyvWatfordChampionship · England | 2–2 | Championship · England |
| 1999-04-24 | HuddersfieldvBarnsleyChampionship · England | 0–1 | Championship · England |
| 1999-04-16 | BarnsleyvSunderlandChampionship · England | 1–3 | Championship · England |
| 1999-04-10 | BarnsleyvTranmereChampionship · England | 1–1 | Championship · England |
| 1999-04-05 | Port ValevBarnsleyChampionship · England | 1–0 | Championship · England |
| 1999-04-03 | BarnsleyvSheffield UnitedChampionship · England | 2–1 | Championship · England |
| 1999-03-28 | PortsmouthvBarnsleyChampionship · England | 1–3 | Championship · England |
| 1999-03-23 | BarnsleyvBristol CityChampionship · England | 2–0 | Championship · England |
| 1999-03-20 | BarnsleyvWolvesChampionship · England | 2–3 | Championship · England |
| 1999-03-13 | BuryvBarnsleyChampionship · England | 0–0 | Championship · England |
| 1999-03-09 | BoltonvBarnsleyChampionship · England | 3–3 | Championship · England |
| 1999-03-03 | BarnsleyvBradfordChampionship · England | 0–1 | Championship · England |
| 1999-02-28 | Crystal PalacevBarnsleyChampionship · England | 1–0 | Championship · England |
| 1999-02-20 | BarnsleyvGrimsbyChampionship · England | 0–0 | Championship · England |
| 1999-02-16 | NorwichvBarnsleyChampionship · England | 0–0 | Championship · England |
| 1999-02-06 | BarnsleyvCreweChampionship · England | 2–2 | Championship · England |
| 1999-01-30 | OxfordvBarnsleyChampionship · England | 1–0 | Championship · England |
| 1999-01-16 | BarnsleyvBirminghamChampionship · England | 0–0 | Championship · England |
| 1999-01-09 | West BromvBarnsleyChampionship · England | 2–0 | Championship · England |