Every competitive match Charlton Athletic played in 1998–99, in Premier League — 42 matches, 10 won, 12 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 | A | Newcastle United | Newcastle United 1998–99 | 0–0 | 36,719 | |
| 22 Aug 1998 | Premier League | H | Southampton | Southampton 1998–99 | 5–0 | John Robinson, Neil Redfearn, Clive Mendonca, Clive Mendonca, Clive Mendonca | 16,488 |
| 29 Aug 1998 | Premier League | A | Arsenal | Arsenal 1998–99 | 0–0 | 38,014 | |
| 9 Sep 1998 | Premier League | A | Manchester United | Manchester United 1998–99 | 1–4 | Mark Kinsella | 55,147 |
| 12 Sep 1998 | Premier League | H | Derby County | Derby County 1998–99 | 1–2 | Clive Mendonca | 19,516 |
| 16 Sep 1998 | League Cup | A | Queens Park Rangers | Queens Park Rangers 1998–99 | 2–0 | Shaun Newton, Lee Harper | 6,497 |
| 19 Sep 1998 | Premier League | A | Liverpool | Liverpool 1998–99 | 3–3 | Richard Rufus, Clive Mendonca, S Jones | 44,526 |
| 22 Sep 1998 | League Cup | H | Queens Park Rangers | Queens Park Rangers 1998–99 | 1–0 | Eddie Youds | 11,726 |
| 26 Sep 1998 | Premier League | H | Coventry City | Coventry City 1998–99 | 1–1 | Andy Hunt | 20,043 |
| 3 Oct 1998 | Premier League | A | Nottingham Forest | Nottingham Forest 1998–99 | 1–0 | Eddie Youds | 22,661 |
| 17 Oct 1998 | Premier League | A | Chelsea | Chelsea 1998–99 | 1–2 | Eddie Youds | 34,639 |
| 24 Oct 1998 | Premier League | H | West Ham United | West Ham United 1998–99 | 4–2 | Carl Tiler, Danny Mills, Andy Hunt, Neil Redfearn | 20,043 |
| 27 Oct 1998 | League Cup | H | Leicester City | Leicester City 1998–99 | 1–2 | Paul Mortimer | 19,671 |
| 2 Nov 1998 | Premier League | A | Tottenham Hotspur | Tottenham Hotspur 1998–99 | 2–2 | Andy Hunt, Andy Hunt | 32,202 |
| 7 Nov 1998 | Premier League | H | Leicester City | Leicester City 1998–99 | 0–0 | 20,021 | |
| 14 Nov 1998 | Premier League | H | Middlesbrough | Middlesbrough 1998–99 | 1–1 | Clive Mendonca | 20,043 |
| 21 Nov 1998 | Premier League | A | Leeds United | Leeds United 1998–99 | 1–4 | Paul Mortimer | 32,487 |
| 28 Nov 1998 | Premier League | H | Everton | Everton 1998–99 | 1–2 | Mark Kinsella | 20,043 |
| 5 Dec 1998 | Premier League | A | Blackburn Rovers | Blackburn Rovers 1998–99 | 0–1 | 22,568 | |
| 12 Dec 1998 | Premier League | A | Sheffield Wednesday | Sheffield Wednesday 1998–99 | 0–3 | 26,010 | |
| 21 Dec 1998 | Premier League | H | Aston Villa | Aston Villa 1998–99 | 0–1 | 20,043 | |
| 26 Dec 1998 | Premier League | A | AFC Wimbledon | AFC Wimbledon 1998–99 | 1–2 | Neil Redfearn | 19,106 |
| 28 Dec 1998 | Premier League | H | Arsenal | Arsenal 1998–99 | 0–1 | 20,043 | |
| 2 Jan 1999 | FA Cup | A | Blackburn Rovers | Blackburn Rovers 1998–99 | 0–2 | 16,631 | |
| 9 Jan 1999 | Premier League | A | Southampton | Southampton 1998–99 | 1–3 | Andy Hunt | 15,222 |
| 17 Jan 1999 | Premier League | H | Newcastle United | Newcastle United 1998–99 | 2–2 | Mark Bright, Martin Pringle | 20,043 |
| 31 Jan 1999 | Premier League | H | Manchester United | Manchester United 1998–99 | 0–1 | 20,043 | |
| 8 Feb 1999 | Premier League | H | AFC Wimbledon | AFC Wimbledon 1998–99 | 2–0 | Martin Pringle, Dean Blackwell | 20,002 |
| 13 Feb 1999 | Premier League | H | Liverpool | Liverpool 1998–99 | 1–0 | Keith Jones | 20,043 |
| 20 Feb 1999 | Premier League | A | Derby County | Derby County 1998–99 | 2–0 | Andy Hunt, Martin Pringle | 27,853 |
| 27 Feb 1999 | Premier League | H | Nottingham Forest | Nottingham Forest 1998–99 | 0–0 | 20,007 | |
| 6 Mar 1999 | Premier League | A | Coventry City | Coventry City 1998–99 | 1–2 | John Robinson | 20,259 |
| 13 Mar 1999 | Premier League | A | Leicester City | Leicester City 1998–99 | 1–1 | Clive Mendonca | 20,220 |
| 3 Apr 1999 | Premier League | H | Chelsea | Chelsea 1998–99 | 0–1 | 20,046 | |
| 5 Apr 1999 | Premier League | A | West Ham United | West Ham United 1998–99 | 1–0 | Graham Stuart | 26,041 |
| 10 Apr 1999 | Premier League | A | Middlesbrough | Middlesbrough 1998–99 | 0–2 | 34,529 | |
| 17 Apr 1999 | Premier League | H | Leeds United | Leeds United 1998–99 | 1–1 | Graham Stuart | 20,043 |
| 20 Apr 1999 | Premier League | H | Tottenham Hotspur | Tottenham Hotspur 1998–99 | 1–4 | Mark Kinsella | 20,043 |
| 24 Apr 1999 | Premier League | A | Everton | Everton 1998–99 | 1–4 | Graham Stuart | 40,089 |
| 1 May 1999 | Premier League | H | Blackburn Rovers | Blackburn Rovers 1998–99 | 0–0 | 20,041 | |
| 8 May 1999 | Premier League | A | Aston Villa | Aston Villa 1998–99 | 4–3 | Gareth Barry, Clive Mendonca, John Robinson, Danny Mills | 37,705 |
| 16 May 1999 | Premier League | H | Sheffield Wednesday | Sheffield Wednesday 1998–99 | 0–1 | 20,043 |
45 of the goals in this season carry a named scorer.
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