1998–99 Sheffield Wednesday F.C. season FA Premier League FA Premier League

| Date_ | Opponent | Venue | Result_ | Attendance |
|---|---|---|---|---|
| 21 November 1998 | Manchester United | H | 3–1 | 39475 |
| 28 November 1998 | Chelsea | A | 1–1 | 34451 |
| 7 December 1998 | Nottingham Forest | H | 3–2 | 19321 |
| 12 December 1998 | Charlton Athletic | H | 3–0 | 26010 |
| 19 December 1998 | Liverpool | A | 0–2 | 40003 |
| 26 December 1998 | Leicester City | H | 0–1 | 33513 |
| 28 December 1998 | Aston Villa | A | 1–2 | 39217 |
| 9 January 1999 | Tottenham Hotspur | H | 0–0 | 28204 |
| 16 January 1999 | West Ham United | A | 4–0 | 25642 |
| 30 January 1999 | Derby County | H | 0–1 | 24440 |
| 6 February 1999 | Leicester City | A | 2–0 | 20113 |
| 20 February 1999 | Blackburn Rovers | A | 4–1 | 24643 |
| 27 February 1999 | Middlesbrough | H | 3–1 | 24534 |