1999–2000 Sheffield Wednesday F.C. season FA Premier League FA Premier League

| Date_ | Opponent | Venue | Result_ | Attendance |
|---|---|---|---|---|
| 6 November 1999 | Watford | H | 2-2 | 21658 |
| 21 November 1999 | West Ham United | A | 3-4 | 23015 |
| 5 December 1999 | Liverpool | A | 1-4 | 42517 |
| 18 December 1999 | Aston Villa | A | 1-2 | 23885 |
| 26 December 1999 | Middlesbrough | H | 1-0 | 28531 |
| 29 December 1999 | Chelsea | A | 0-3 | 32938 |
| 3 January 2000 | Arsenal | H | 1-1 | 26155 |
| 15 January 2000 | Bradford City | H | 2-0 | 24682 |
| 22 January 2000 | Tottenham Hotspur | A | 1-0 | 35897 |
| 2 February 2000 | Manchester United | H | 0-1 | 39640 |
| 5 February 2000 | Derby County | A | 3-3 | 30100 |
| 12 February 2000 | Southampton | H | 0-1 | 23470 |
| 26 February 2000 | Newcastle United | H | 0-2 | 29212 |
| 4 March 2000 | Everton | A | 1-1 | 32020 |