| 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 |
| 1998-12-28 | Port ValevBoltonChampionship · England | 0–2 | Championship · England |
| 1998-12-26 | BoltonvBradfordChampionship · England | 0–0 | Championship · England |
| 1998-12-19 | BoltonvPortsmouthChampionship · England | 3–1 | Championship · England |
| 1998-12-12 | TranmerevBoltonChampionship · England | 1–1 | Championship · England |
| 1998-12-05 | WolvesvBoltonChampionship · England | 1–1 | Championship · England |
| 1998-11-28 | BoltonvBuryChampionship · England | 4–0 | Championship · England |
| 1998-11-24 | StockportvBoltonChampionship · England | 0–1 | Championship · England |
| 1998-11-21 | IpswichvBoltonChampionship · England | 0–1 | Championship · England |
| 1998-11-14 | BoltonvTranmereChampionship · England | 2–2 | Championship · England |
| 1998-11-07 | QPRvBoltonChampionship · England | 2–0 | Championship · England |
| 1998-11-04 | BoltonvPort ValeChampionship · England | 3–1 | Championship · England |
| 1998-11-01 | BoltonvSunderlandChampionship · England | 0–3 | Championship · England |
| 1998-10-23 | Bristol CityvBoltonChampionship · England | 2–1 | Championship · England |
| 1998-10-20 | BoltonvWatfordChampionship · England | 1–2 | Championship · England |
| 1998-10-17 | BoltonvOxfordChampionship · England | 1–1 | Championship · England |
| 1998-10-03 | BarnsleyvBoltonChampionship · England | 2–2 | Championship · England |
| 1998-09-29 | BoltonvSwindonChampionship · England | 2–1 | Championship · England |
| 1998-09-26 | BoltonvHuddersfieldChampionship · England | 3–0 | Championship · England |
| 1998-09-19 | CrewevBoltonChampionship · England | 4–4 | Championship · England |
| 1998-09-12 | BoltonvBirminghamChampionship · England | 3–1 | Championship · England |
| 1998-09-08 | West BromvBoltonChampionship · England | 2–3 | Championship · England |
| 1998-08-29 | BoltonvSheffield UnitedChampionship · England | 2–2 | Championship · England |
| 1998-08-23 | BradfordvBoltonChampionship · England | 2–2 | Championship · England |
| 1998-08-15 | BoltonvGrimsbyChampionship · England | 2–0 | Championship · England |
| 1998-08-08 | Crystal PalacevBoltonChampionship · England | 2–2 | Championship · England |
| 1998-05-10 | ChelseavBoltonPremier League · England | 2–0 | Premier League · England |
| 1998-05-02 | BoltonvCrystal PalacePremier League · England | 5–2 | Premier League · England |
| 1998-04-25 | Aston VillavBoltonPremier League · England | 1–3 | Premier League · England |