Every competitive match West Ham United played in 1998–99, in Premier League — 42 matches, 17 won, 10 drawn, 15 lost, with scorers and attendances where the record holds them.
| Date | Competition | Venue | Opponent | Their season | Score | Scorers | Att |
|---|---|---|---|---|---|---|---|
| 15 Aug 1998 | Premier League | A | Sheffield Wednesday | Sheffield Wednesday 1998–99 | 1–0 | Ian Wright | 30,236 |
| 22 Aug 1998 | Premier League | H | Manchester United | Manchester United 1998–99 | 0–0 | 26,039 | |
| 29 Aug 1998 | Premier League | A | Coventry City | Coventry City 1998–99 | 0–0 | 20,818 | |
| 9 Sep 1998 | Premier League | H | Wimbledon | Wimbledon 1998–99 | 3–4 | John Hartson, Ian Wright | 25,311 |
| 12 Sep 1998 | Premier League | H | Liverpool | Liverpool 1998–99 | 2–1 | John Hartson, Eyal Berkovic | 26,029 |
| 15 Sep 1998 | League Cup | A | Northampton Town | Northampton Town 1998–99 | 0–2 | 7,254 | |
| 19 Sep 1998 | Premier League | A | Nottingham Forest | Nottingham Forest 1998–99 | 0–0 | 26,463 | |
| 22 Sep 1998 | League Cup | H | Northampton Town | Northampton Town 1998–99 | 1–0 | Frank Lampard | 25,435 |
| 28 Sep 1998 | Premier League | H | Southampton | Southampton 1998–99 | 1–0 | Ian Wright | 23,153 |
| 3 Oct 1998 | Premier League | A | Blackburn Rovers | Blackburn Rovers 1998–99 | 0–3 | 25,213 | |
| 17 Oct 1998 | Premier League | H | Aston Villa | Aston Villa 1998–99 | 0–0 | 26,002 | |
| 24 Oct 1998 | Premier League | A | Charlton Athletic | Charlton Athletic 1998–99 | 2–4 | Richard Rufus 0, Eyal Berkovic | 20,043 |
| 31 Oct 1998 | Premier League | A | Newcastle United | Newcastle United 1998–99 | 3–0 | Ian Wright, Trevor Sinclair | 36,744 |
| 8 Nov 1998 | Premier League | H | Chelsea | Chelsea 1998–99 | 1–1 | Neil Ruddock | 26,023 |
| 14 Nov 1998 | Premier League | H | Leicester City | Leicester City 1998–99 | 3–2 | Paul Kitson, Steve Lomas, Frank Lampard, Jr | 25,642 |
| 22 Nov 1998 | Premier League | A | Derby County | Derby County 1998–99 | 2–0 | John Hartson, Marc Keller | 31,366 |
| 28 Nov 1998 | Premier League | H | Tottenham Hotspur | Tottenham Hotspur 1998–99 | 2–1 | Trevor Sinclair | 26,044 |
| 5 Dec 1998 | Premier League | A | Leeds United | Leeds United 1998–99 | 0–4 | 36,320 | |
| 12 Dec 1998 | Premier League | A | Middlesbrough | Middlesbrough 1998–99 | 0–1 | 34,623 | |
| 19 Dec 1998 | Premier League | H | Everton | Everton 1998–99 | 2–1 | Marc Keller, Trevor Sinclair | 25,998 |
| 26 Dec 1998 | Premier League | A | Arsenal | Arsenal 1998–99 | 0–1 | 38,098 | |
| 28 Dec 1998 | Premier League | H | Coventry City | Coventry City 1998–99 | 2–0 | 25,662 | |
| 2 Jan 1999 | FA Cup | H | Swansea City | Swansea City 1998–99 | 1–1 | Julian Dicks | 26,039 |
| 10 Jan 1999 | Premier League | A | Manchester United | Manchester United 1998–99 | 1–4 | Frank Lampard, Jr | 55,180 |
| 13 Jan 1999 | FA Cup | A | Swansea City | Swansea City 1998–99 | 0–1 | 10,116 | |
| 16 Jan 1999 | Premier League | H | Sheffield Wednesday | Sheffield Wednesday 1998–99 | 0–4 | 25,642 | |
| 30 Jan 1999 | Premier League | A | Wimbledon | Wimbledon 1998–99 | 0–0 | 23,035 | |
| 6 Feb 1999 | Premier League | H | Arsenal | Arsenal 1998–99 | 0–4 | 26,042 | |
| 13 Feb 1999 | Premier League | H | Nottingham Forest | Nottingham Forest 1998–99 | 2–1 | Ian Pearce, Frank Lampard, Jr | 25,458 |
| 20 Feb 1999 | Premier League | A | Liverpool | Liverpool 1998–99 | 2–2 | Frank Lampard, Jr 0, Marc Keller | 44,511 |
| 27 Feb 1999 | Premier League | H | Blackburn Rovers | Blackburn Rovers 1998–99 | 2–0 | Ian Pearce, Paolo Di Canio | 25,529 |
| 6 Mar 1999 | Premier League | A | Southampton | Southampton 1998–99 | 0–1 | 15,240 | |
| 13 Mar 1999 | Premier League | A | Chelsea | Chelsea 1998–99 | 1–0 | Paul Kitson | 34,765 |
| 20 Mar 1999 | Premier League | H | Newcastle United | Newcastle United 1998–99 | 2–0 | Paolo Di Canio, Paul Kitson | 25,997 |
| 2 Apr 1999 | Premier League | A | Aston Villa | Aston Villa 1998–99 | 0–0 | 36,813 | |
| 5 Apr 1999 | Premier League | H | Charlton Athletic | Charlton Athletic 1998–99 | 0–1 | 26,041 | |
| 10 Apr 1999 | Premier League | A | Leicester City | Leicester City 1998–99 | 0–0 | 20,402 | |
| 17 Apr 1999 | Premier League | H | Derby County | Derby County 1998–99 | 5–1 | Paolo Di Canio, Eyal Berkovic, Ian Wright, Neil Ruddock, Trevor Sinclair | 25,485 |
| 24 Apr 1999 | Premier League | A | Tottenham Hotspur | Tottenham Hotspur 1998–99 | 2–1 | Ian Wright, Marc Keller | 36,089 |
| 1 May 1999 | Premier League | H | Leeds United | Leeds United 1998–99 | 1–5 | Paolo Di Canio | 25,997 |
| 8 May 1999 | Premier League | A | Everton | Everton 1998–99 | 0–6 | 40,049 | |
| 16 May 1999 | Premier League | H | Middlesbrough | Middlesbrough 1998–99 | 4–0 | Frank Lampard, Jr, Marc Keller, Trevor Sinclair, Paolo Di Canio | 25,902 |
43 of the goals in this season carry a named scorer.
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