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

| Date_ | Opponent | Venue | Result_ | Attendance |
|---|---|---|---|---|
| 7 August 1999 | Liverpool | H | 1-2 | 34853 |
| 11 August 1999 | Manchester United | A | 0-4 | 54941 |
| 14 August 1999 | Bradford City | A | 1-1 | 18276 |
| 21 August 1999 | Tottenham Hotspur | H | 1-2 | 24027 |
| 25 August 1999 | Derby County | H | 0-2 | 20943 |
| 28 August 1999 | Southampton | A | 0-2 | 14815 |
| 11 September 1999 | Everton | H | 0-2 | 23539 |
| 19 September 1999 | Newcastle United | A | 0-8 | 36619 |
| 25 September 1999 | Sunderland | A | 0-1 | 41132 |
| 2 October 1999 | Wimbledon | H | 5-1 | 18077 |
| 16 October 1999 | Leeds United | A | 0-2 | 39437 |
| 23 October 1999 | Coventry City | H | 0-0 | 23296 |
| 30 October 1999 | Leicester City | A | 0-3 | 19046 |