Every competitive match Sheffield Wednesday played in 1998–99, in Premier League — 43 matches, 15 won, 8 drawn, 20 lost, with scorers and attendances where the record holds them.
| Date | Competition | Venue | Opponent | Their season | Score | Scorers | Att |
|---|---|---|---|---|---|---|---|
| 15 Aug 1998 | Premier League | H | West Ham United | West Ham United 1998–99 | 0–1 | 30,236 | |
| 22 Aug 1998 | Premier League | A | Tottenham Hotspur | Tottenham Hotspur 1998–99 | 3–0 | Peter Atherton, Paolo Di Canio, Andy Hinchcliffe | 32,129 |
| 29 Aug 1998 | Premier League | H | Aston Villa | Aston Villa 1998–99 | 0–1 | 25,989 | |
| 9 Sep 1998 | Premier League | A | Derby County | Derby County 1998–99 | 0–1 | 26,209 | |
| 12 Sep 1998 | Premier League | H | Blackburn Rovers | Blackburn Rovers 1998–99 | 3–0 | Peter Atherton, Andy Hinchcliffe, Paolo Di Canio | 20,846 |
| 16 Sep 1998 | League Cup | H | Cambridge United | Cambridge United 1998–99 | 0–1 | 8,921 | |
| 19 Sep 1998 | Premier League | A | Wimbledon | Wimbledon 1998–99 | 1–2 | Paolo Di Canio | 13,163 |
| 22 Sep 1998 | League Cup | A | Cambridge United | Cambridge United 1998–99 | 1–1 | Jamie Campbell | 8,502 |
| 26 Sep 1998 | Premier League | H | Arsenal | Arsenal 1998–99 | 1–0 | Lee Briscoe | 27,949 |
| 3 Oct 1998 | Premier League | A | Middlesbrough | Middlesbrough 1998–99 | 0–4 | 34,163 | |
| 18 Oct 1998 | Premier League | A | Coventry City | Coventry City 1998–99 | 0–1 | 16,006 | |
| 24 Oct 1998 | Premier League | H | Everton | Everton 1998–99 | 0–0 | 26,592 | |
| 31 Oct 1998 | Premier League | H | Southampton | Southampton 1998–99 | 0–0 | 30,078 | |
| 8 Nov 1998 | Premier League | A | Leeds United | Leeds United 1998–99 | 1–2 | Andy Booth | 30,012 |
| 14 Nov 1998 | Premier League | A | Newcastle United | Newcastle United 1998–99 | 1–1 | Petter Rudi | 36,698 |
| 21 Nov 1998 | Premier League | H | Manchester United | Manchester United 1998–99 | 3–1 | Niclas Alexandersson, Niclas Alexandersson, Wim Jonk | 39,475 |
| 28 Nov 1998 | Premier League | A | Chelsea | Chelsea 1998–99 | 1–1 | Andy Booth | 34,451 |
| 7 Dec 1998 | Premier League | H | Nottingham Forest | Nottingham Forest 1998–99 | 3–2 | Niclas Alexandersson, Benito Carbone, Benito Carbone | 19,321 |
| 12 Dec 1998 | Premier League | H | Charlton Athletic | Charlton Athletic 1998–99 | 3–0 | Andy Booth, Benito Carbone, Petter Rudi | 26,010 |
| 19 Dec 1998 | Premier League | A | Liverpool | Liverpool 1998–99 | 0–2 | 40,003 | |
| 26 Dec 1998 | Premier League | H | Leicester City | Leicester City 1998–99 | 0–1 | 33,513 | |
| 28 Dec 1998 | Premier League | A | Aston Villa | Aston Villa 1998–99 | 1–2 | Benito Carbone | 39,217 |
| 3 Jan 1999 | FA Cup | H | Norwich City | Norwich City 1998–99 | 4–1 | Ritchie Humphreys, Ritchie Humphreys, Petter Rudi, Dejan Stefanović | 18,737 |
| 9 Jan 1999 | Premier League | H | Tottenham Hotspur | Tottenham Hotspur 1998–99 | 0–0 | 28,204 | |
| 16 Jan 1999 | Premier League | A | West Ham United | West Ham United 1998–99 | 4–0 | Andy Hinchcliffe, Petter Rudi, Ritchie Humphreys, Benito Carbone | 25,642 |
| 23 Jan 1999 | FA Cup | H | Stockport County | Stockport County 1998–99 | 2–0 | Emerson Thome, Benito Carbone | 20,984 |
| 30 Jan 1999 | Premier League | H | Derby County | Derby County 1998–99 | 0–1 | 24,440 | |
| 6 Feb 1999 | Premier League | A | Leicester City | Leicester City 1998–99 | 2–0 | Wim Jonk, Benito Carbone | 20,113 |
| 13 Feb 1999 | FA Cup | H | Chelsea | Chelsea 1998–99 | 0–1 | 29,410 | |
| 20 Feb 1999 | Premier League | A | Blackburn Rovers | Blackburn Rovers 1998–99 | 4–1 | Danny Sonner, Petter Rudi, Petter Rudi, Andy Booth | 24,643 |
| 27 Feb 1999 | Premier League | H | Middlesbrough | Middlesbrough 1998–99 | 3–1 | Andy Booth, Andy Booth, Danny Sonner | 24,534 |
| 3 Mar 1999 | Premier League | H | Wimbledon | Wimbledon 1998–99 | 1–2 | Emerson Thome | 24,116 |
| 9 Mar 1999 | Premier League | A | Arsenal | Arsenal 1998–99 | 0–3 | 37,792 | |
| 13 Mar 1999 | Premier League | H | Leeds United | Leeds United 1998–99 | 0–2 | 28,142 | |
| 20 Mar 1999 | Premier League | A | Southampton | Southampton 1998–99 | 0–1 | 15,201 | |
| 3 Apr 1999 | Premier League | H | Coventry City | Coventry City 1998–99 | 1–2 | Petter Rudi | 28,136 |
| 5 Apr 1999 | Premier League | A | Everton | Everton 1998–99 | 2–1 | Benito Carbone, Benito Carbone | 35,270 |
| 17 Apr 1999 | Premier League | A | Manchester United | Manchester United 1998–99 | 0–3 | 55,270 | |
| 21 Apr 1999 | Premier League | H | Newcastle United | Newcastle United 1998–99 | 1–1 | Philip Scott | 21,545 |
| 25 Apr 1999 | Premier League | H | Chelsea | Chelsea 1998–99 | 0–0 | 21,652 | |
| 1 May 1999 | Premier League | A | Nottingham Forest | Nottingham Forest 1998–99 | 0–2 | 20,480 | |
| 8 May 1999 | Premier League | H | Liverpool | Liverpool 1998–99 | 1–0 | Richard Cresswell | 27,383 |
| 16 May 1999 | Premier League | A | Charlton Athletic | Charlton Athletic 1998–99 | 1–0 | Danny Sonner | 20,043 |
48 of the goals in this season carry a named scorer.
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