| 1999-12-28 | WatfordvSouthamptonPremier League · England | 3–2 | Premier League · England |
| 1999-12-26 | TottenhamvWatfordPremier League · England | 4–0 | Premier League · England |
| 1999-12-18 | WatfordvEvertonPremier League · England | 1–3 | Premier League · England |
| 1999-12-04 | WimbledonvWatfordPremier League · England | 5–0 | Premier League · England |
| 1999-11-27 | WatfordvSunderlandPremier League · England | 2–3 | Premier League · England |
| 1999-11-20 | WatfordvNewcastlePremier League · England | 1–1 | Premier League · England |
| 1999-11-06 | Sheffield WedsvWatfordPremier League · England | 2–2 | Premier League · England |
| 1999-10-31 | CoventryvWatfordPremier League · England | 4–0 | Premier League · England |
| 1999-10-24 | WatfordvMiddlesbroughPremier League · England | 1–3 | Premier League · England |
| 1999-10-16 | Man UnitedvWatfordPremier League · England | 4–1 | Premier League · England |
| 1999-10-03 | WatfordvLeedsPremier League · England | 1–2 | Premier League · England |
| 1999-09-25 | ArsenalvWatfordPremier League · England | 1–0 | Premier League · England |
| 1999-09-18 | WatfordvChelseaPremier League · England | 1–0 | Premier League · England |
| 1999-09-11 | West HamvWatfordPremier League · England | 1–0 | Premier League · England |
| 1999-08-30 | LeicestervWatfordPremier League · England | 1–0 | Premier League · England |
| 1999-08-24 | WatfordvAston VillaPremier League · England | 0–1 | Premier League · England |
| 1999-08-21 | WatfordvBradfordPremier League · England | 1–0 | Premier League · England |
| 1999-08-14 | LiverpoolvWatfordPremier League · England | 0–1 | Premier League · England |
| 1999-08-10 | SunderlandvWatfordPremier League · England | 2–0 | Premier League · England |
| 1999-08-07 | WatfordvWimbledonPremier League · England | 2–3 | Premier League · England |
| 1999-05-09 | WatfordvGrimsbyChampionship · England | 1–0 | Championship · England |
| 1999-05-01 | BarnsleyvWatfordChampionship · England | 2–2 | Championship · England |
| 1999-04-27 | Port ValevWatfordChampionship · England | 1–2 | Championship · England |
| 1999-04-24 | WatfordvCrystal PalaceChampionship · England | 2–1 | Championship · England |
| 1999-04-17 | CrewevWatfordChampionship · England | 0–1 | Championship · England |
| 1999-04-10 | WatfordvBoltonChampionship · England | 2–0 | Championship · England |
| 1999-04-05 | BirminghamvWatfordChampionship · England | 1–2 | Championship · England |
| 1999-04-03 | WatfordvTranmereChampionship · England | 2–1 | Championship · England |
| 1999-03-20 | WatfordvBuryChampionship · England | 0–0 | Championship · England |
| 1999-03-13 | OxfordvWatfordChampionship · England | 0–0 | Championship · England |
| 1999-03-06 | Sheffield UnitedvWatfordChampionship · England | 3–0 | Championship · England |
| 1999-03-02 | IpswichvWatfordChampionship · England | 3–2 | Championship · England |
| 1999-02-26 | WatfordvSwindonChampionship · England | 0–1 | Championship · England |
| 1999-02-20 | QPRvWatfordChampionship · England | 1–2 | Championship · England |
| 1999-02-16 | WatfordvHuddersfieldChampionship · England | 1–1 | Championship · England |
| 1999-02-06 | BradfordvWatfordChampionship · England | 2–0 | Championship · England |
| 1999-01-30 | WatfordvSunderlandChampionship · England | 2–1 | Championship · England |
| 1999-01-23 | WatfordvWest BromChampionship · England | 0–2 | Championship · England |
| 1999-01-16 | WolvesvWatfordChampionship · England | 0–0 | Championship · England |
| 1999-01-09 | WatfordvPortsmouthChampionship · England | 0–0 | Championship · England |