| 1999-12-28 | BoltonvWest BromChampionship · England | 1–1 | Championship · England |
| 1999-12-18 | BoltonvStockportChampionship · England | 0–1 | Championship · England |
| 1999-12-07 | BlackburnvBoltonChampionship · England | 3–1 | Championship · England |
| 1999-12-04 | BoltonvTranmereChampionship · England | 2–3 | Championship · England |
| 1999-11-27 | PortsmouthvBoltonChampionship · England | 0–0 | Championship · England |
| 1999-11-23 | FulhamvBoltonChampionship · England | 1–1 | Championship · England |
| 1999-11-20 | BoltonvGrimsbyChampionship · England | 2–0 | Championship · England |
| 1999-11-14 | Sheffield UnitedvBoltonChampionship · England | 1–2 | Championship · England |
| 1999-11-06 | BoltonvCrystal PalaceChampionship · England | 2–0 | Championship · England |
| 1999-10-30 | BoltonvSwindonChampionship · England | 2–0 | Championship · England |
| 1999-10-27 | Nott'm ForestvBoltonChampionship · England | 1–1 | Championship · England |
| 1999-10-24 | NorwichvBoltonChampionship · England | 2–1 | Championship · England |
| 1999-10-19 | BoltonvCreweChampionship · England | 2–2 | Championship · England |
| 1999-10-16 | BoltonvHuddersfieldChampionship · England | 1–0 | Championship · England |
| 1999-10-09 | WolvesvBoltonChampionship · England | 1–0 | Championship · England |
| 1999-10-02 | SwindonvBoltonChampionship · England | 0–4 | Championship · England |
| 1999-09-25 | BoltonvNott'm ForestChampionship · England | 3–2 | Championship · England |
| 1999-09-18 | BoltonvBarnsleyChampionship · England | 2–2 | Championship · England |
| 1999-09-11 | CharltonvBoltonChampionship · England | 2–1 | Championship · England |
| 1999-09-05 | BoltonvBirminghamChampionship · England | 3–3 | Championship · England |
| 1999-08-28 | BoltonvMan CityChampionship · England | 0–1 | Championship · England |
| 1999-08-21 | IpswichvBoltonChampionship · England | 1–0 | Championship · England |
| 1999-08-14 | BoltonvQPRChampionship · England | 2–1 | Championship · England |
| 1999-08-07 | TranmerevBoltonChampionship · England | 0–0 | Championship · England |
| 1999-05-09 | PortsmouthvBoltonChampionship · England | 0–2 | Championship · England |
| 1999-04-30 | BoltonvWolvesChampionship · England | 1–1 | Championship · England |
| 1999-04-23 | BuryvBoltonChampionship · England | 2–1 | Championship · England |
| 1999-04-20 | NorwichvBoltonChampionship · England | 2–2 | Championship · England |
| 1999-04-17 | BoltonvIpswichChampionship · England | 2–0 | Championship · England |
| 1999-04-13 | BoltonvBristol CityChampionship · England | 1–0 | Championship · England |
| 1999-04-10 | WatfordvBoltonChampionship · England | 2–0 | Championship · England |
| 1999-04-05 | BoltonvStockportChampionship · England | 1–2 | Championship · England |
| 1999-04-03 | OxfordvBoltonChampionship · England | 0–0 | Championship · England |
| 1999-03-20 | SunderlandvBoltonChampionship · England | 3–1 | Championship · England |
| 1999-03-13 | BoltonvQPRChampionship · England | 2–1 | Championship · England |
| 1999-03-09 | BoltonvBarnsleyChampionship · England | 3–3 | Championship · England |
| 1999-03-06 | SwindonvBoltonChampionship · England | 3–3 | Championship · England |
| 1999-03-02 | HuddersfieldvBoltonChampionship · England | 3–2 | Championship · England |
| 1999-02-27 | BoltonvCreweChampionship · England | 1–3 | Championship · England |
| 1999-02-21 | BirminghamvBoltonChampionship · England | 0–0 | Championship · England |
| 1999-02-13 | BoltonvWest BromChampionship · England | 2–1 | Championship · England |
| 1999-02-06 | GrimsbyvBoltonChampionship · England | 0–1 | Championship · England |
| 1999-01-30 | BoltonvNorwichChampionship · England | 2–0 | Championship · England |
| 1999-01-16 | Sheffield UnitedvBoltonChampionship · England | 1–2 | Championship · England |
| 1999-01-10 | BoltonvCrystal PalaceChampionship · England | 3–0 | Championship · England |