| 1999-12-28 | LiverpoolvWimbledonPremier League · England | 3–1 | Premier League · England |
| 1999-12-26 | NewcastlevLiverpoolPremier League · England | 2–2 | Premier League · England |
| 1999-12-18 | LiverpoolvCoventryPremier League · England | 2–0 | Premier League · England |
| 1999-12-05 | LiverpoolvSheffield WedsPremier League · England | 4–1 | Premier League · England |
| 1999-11-27 | West HamvLiverpoolPremier League · England | 1–0 | Premier League · England |
| 1999-11-20 | SunderlandvLiverpoolPremier League · England | 0–2 | Premier League · England |
| 1999-11-06 | LiverpoolvDerbyPremier League · England | 2–0 | Premier League · England |
| 1999-11-01 | LiverpoolvBradfordPremier League · England | 3–1 | Premier League · England |
| 1999-10-27 | LiverpoolvWest HamPremier League · England | 1–0 | Premier League · England |
| 1999-10-23 | SouthamptonvLiverpoolPremier League · England | 1–1 | Premier League · England |
| 1999-10-16 | LiverpoolvChelseaPremier League · England | 1–0 | Premier League · England |
| 1999-10-02 | Aston VillavLiverpoolPremier League · England | 0–0 | Premier League · England |
| 1999-09-27 | LiverpoolvEvertonPremier League · England | 0–1 | Premier League · England |
| 1999-09-18 | LeicestervLiverpoolPremier League · England | 2–2 | Premier League · England |
| 1999-09-11 | LiverpoolvMan UnitedPremier League · England | 2–3 | Premier League · England |
| 1999-08-28 | LiverpoolvArsenalPremier League · England | 2–0 | Premier League · England |
| 1999-08-23 | LeedsvLiverpoolPremier League · England | 1–2 | Premier League · England |
| 1999-08-21 | MiddlesbroughvLiverpoolPremier League · England | 1–0 | Premier League · England |
| 1999-08-14 | LiverpoolvWatfordPremier League · England | 0–1 | Premier League · England |
| 1999-08-07 | Sheffield WedsvLiverpoolPremier League · England | 1–2 | Premier League · England |
| 1999-05-16 | LiverpoolvWimbledonPremier League · England | 3–0 | Premier League · England |
| 1999-05-08 | Sheffield WedsvLiverpoolPremier League · England | 1–0 | Premier League · England |
| 1999-05-05 | LiverpoolvMan UnitedPremier League · England | 2–2 | Premier League · England |
| 1999-05-01 | LiverpoolvTottenhamPremier League · England | 3–2 | Premier League · England |
| 1999-04-24 | BlackburnvLiverpoolPremier League · England | 1–3 | Premier League · England |
| 1999-04-21 | LiverpoolvLeicesterPremier League · England | 0–1 | Premier League · England |
| 1999-04-17 | LiverpoolvAston VillaPremier League · England | 0–1 | Premier League · England |
| 1999-04-12 | LeedsvLiverpoolPremier League · England | 0–0 | Premier League · England |
| 1999-04-05 | Nott'm ForestvLiverpoolPremier League · England | 2–2 | Premier League · England |
| 1999-04-03 | LiverpoolvEvertonPremier League · England | 3–2 | Premier League · England |
| 1999-03-13 | DerbyvLiverpoolPremier League · England | 3–2 | Premier League · England |
| 1999-02-27 | ChelseavLiverpoolPremier League · England | 2–1 | Premier League · England |
| 1999-02-20 | LiverpoolvWest HamPremier League · England | 2–2 | Premier League · England |
| 1999-02-13 | CharltonvLiverpoolPremier League · England | 1–0 | Premier League · England |
| 1999-02-06 | LiverpoolvMiddlesbroughPremier League · England | 3–1 | Premier League · England |
| 1999-01-30 | CoventryvLiverpoolPremier League · England | 2–1 | Premier League · England |
| 1999-01-16 | LiverpoolvSouthamptonPremier League · England | 7–1 | Premier League · England |
| 1999-01-09 | ArsenalvLiverpoolPremier League · England | 0–0 | Premier League · England |