| 1999-12-28 | TranmerevSwindonChampionship · England | 3–1 | Championship · England |
| 1999-12-26 | WalsallvTranmereChampionship · England | 1–2 | Championship · England |
| 1999-12-17 | TranmerevNorwichChampionship · England | 1–2 | Championship · England |
| 1999-12-04 | BoltonvTranmereChampionship · England | 2–3 | Championship · England |
| 1999-11-27 | TranmerevWolvesChampionship · England | 1–0 | Championship · England |
| 1999-11-23 | BirminghamvTranmereChampionship · England | 3–1 | Championship · England |
| 1999-11-20 | TranmerevNott'm ForestChampionship · England | 3–0 | Championship · England |
| 1999-11-12 | IpswichvTranmereChampionship · England | 0–0 | Championship · England |
| 1999-11-06 | TranmerevWest BromChampionship · England | 3–0 | Championship · England |
| 1999-10-30 | TranmerevCreweChampionship · England | 2–0 | Championship · England |
| 1999-10-26 | CharltonvTranmereChampionship · England | 3–2 | Championship · England |
| 1999-10-23 | Crystal PalacevTranmereChampionship · England | 2–2 | Championship · England |
| 1999-10-19 | TranmerevGrimsbyChampionship · England | 3–2 | Championship · England |
| 1999-10-16 | TranmerevMan CityChampionship · England | 1–1 | Championship · England |
| 1999-10-09 | QPRvTranmereChampionship · England | 2–1 | Championship · England |
| 1999-10-03 | CrewevTranmereChampionship · England | 0–2 | Championship · England |
| 1999-09-25 | TranmerevCharltonChampionship · England | 2–2 | Championship · England |
| 1999-09-18 | TranmerevPortsmouthChampionship · England | 2–4 | Championship · England |
| 1999-09-11 | BlackburnvTranmereChampionship · England | 2–0 | Championship · England |
| 1999-09-03 | BarnsleyvTranmereChampionship · England | 3–0 | Championship · England |
| 1999-08-30 | TranmerevSheffield UnitedChampionship · England | 1–3 | Championship · England |
| 1999-08-28 | Port ValevTranmereChampionship · England | 1–0 | Championship · England |
| 1999-08-21 | TranmerevHuddersfieldChampionship · England | 1–0 | Championship · England |
| 1999-08-14 | StockportvTranmereChampionship · England | 2–1 | Championship · England |
| 1999-08-07 | TranmerevBoltonChampionship · England | 0–0 | Championship · England |
| 1999-05-09 | TranmerevWest BromChampionship · England | 3–1 | Championship · England |
| 1999-05-01 | GrimsbyvTranmereChampionship · England | 1–0 | Championship · England |
| 1999-04-24 | TranmerevPort ValeChampionship · England | 1–1 | Championship · England |
| 1999-04-17 | NorwichvTranmereChampionship · England | 2–2 | Championship · England |
| 1999-04-10 | BarnsleyvTranmereChampionship · England | 1–1 | Championship · England |
| 1999-04-05 | TranmerevOxfordChampionship · England | 2–2 | Championship · England |
| 1999-04-03 | WatfordvTranmereChampionship · England | 2–1 | Championship · England |
| 1999-03-26 | TranmerevCreweChampionship · England | 3–0 | Championship · England |
| 1999-03-20 | StockportvTranmereChampionship · England | 0–0 | Championship · England |
| 1999-03-13 | TranmerevSheffield UnitedChampionship · England | 2–3 | Championship · England |
| 1999-03-09 | TranmerevBirminghamChampionship · England | 0–1 | Championship · England |
| 1999-03-06 | IpswichvTranmereChampionship · England | 1–0 | Championship · England |
| 1999-03-03 | SwindonvTranmereChampionship · England | 2–3 | Championship · England |
| 1999-02-27 | TranmerevBuryChampionship · England | 4–0 | Championship · England |
| 1999-02-20 | HuddersfieldvTranmereChampionship · England | 0–0 | Championship · England |
| 1999-02-13 | TranmerevQPRChampionship · England | 3–2 | Championship · England |
| 1999-02-06 | PortsmouthvTranmereChampionship · England | 1–1 | Championship · England |
| 1999-01-30 | TranmerevCrystal PalaceChampionship · England | 3–1 | Championship · England |
| 1999-01-16 | Bristol CityvTranmereChampionship · England | 1–1 | Championship · England |
| 1999-01-08 | TranmerevWolvesChampionship · England | 1–2 | Championship · England |