1999–2000 Manchester United F.C. season Premier League Premier League

| Date_ | Opponents | H_A | Result_F_A | Attendance | League_position |
|---|---|---|---|---|---|
| 8 August 1999 | Everton | A | 1–1 | 39141 | 9th |
| 11 August 1999 | Sheffield Wednesday | H | 4–0 | 54941 | 3rd |
| 14 August 1999 | Leeds United | H | 2–0 | 55187 | 1st |
| 22 August 1999 | Arsenal | A | 2–1 | 38147 | 1st |
| 25 August 1999 | Coventry City | A | 2–1 | 22024 | 1st |
| 30 August 1999 | Newcastle United | H | 5–1 | 55190 | 1st |
| 11 September 1999 | Liverpool | A | 3–2 | 44929 | 1st |
| 18 September 1999 | Wimbledon | H | 1–1 | 55189 | 1st |
| 25 September 1999 | Southampton | H | 3–3 | 55249 | 1st |
| 3 October 1999 | Chelsea | A | 0–5 | 34909 | 2nd |
| 16 October 1999 | Watford | H | 4–1 | 55188 | 2nd |