Every competitive match Coventry City played in 1998–99, in Premier League — 44 matches, 15 won, 9 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 | Chelsea | Chelsea 1998–99 | 2–1 | Darren Huckerby, Dion Dublin | 23,042 |
| 22 Aug 1998 | Premier League | A | Nottingham Forest | Nottingham Forest 1998–99 | 0–1 | 22,546 | |
| 29 Aug 1998 | Premier League | H | West Ham United | West Ham United 1998–99 | 0–0 | 20,818 | |
| 9 Sep 1998 | Premier League | A | Liverpool | Liverpool 1998–99 | 0–2 | 41,771 | |
| 12 Sep 1998 | Premier League | A | Manchester United | Manchester United 1998–99 | 0–2 | 55,193 | |
| 16 Sep 1998 | League Cup | H | Southend United | 1–0 | Paul Hall | 6,631 | |
| 19 Sep 1998 | Premier League | H | Newcastle United | Newcastle United 1998–99 | 1–5 | Noel Whelan | 22,656 |
| 22 Sep 1998 | League Cup | A | Southend United | 4–0 | George Boateng, Dion Dublin, Noel Whelan, Trond Egil Soltvedt | 6,292 | |
| 26 Sep 1998 | Premier League | A | Charlton Athletic | Charlton Athletic 1998–99 | 1–1 | Noel Whelan | 20,043 |
| 3 Oct 1998 | Premier League | H | Aston Villa | Aston Villa 1998–99 | 1–2 | Trond Egil Soltvedt | 22,654 |
| 18 Oct 1998 | Premier League | H | Sheffield Wednesday | Sheffield Wednesday 1998–99 | 1–0 | Dion Dublin | 16,006 |
| 24 Oct 1998 | Premier League | A | Southampton | Southampton 1998–99 | 1–2 | Dion Dublin | 15,152 |
| 27 Oct 1998 | League Cup | A | Luton Town | Luton Town 1998–99 | 0–2 | 9,051 | |
| 31 Oct 1998 | Premier League | H | Arsenal | Arsenal 1998–99 | 0–1 | 23,040 | |
| 7 Nov 1998 | Premier League | A | Blackburn Rovers | Blackburn Rovers 1998–99 | 2–1 | Darren Huckerby, Noel Whelan | 23,779 |
| 15 Nov 1998 | Premier League | H | Everton | Everton 1998–99 | 3–0 | Steve Froggatt, Darren Huckerby, Noel Whelan | 19,290 |
| 21 Nov 1998 | Premier League | A | Middlesbrough | Middlesbrough 1998–99 | 0–2 | 34,293 | |
| 28 Nov 1998 | Premier League | H | Leicester City | Leicester City 1998–99 | 1–1 | Darren Huckerby | 19,894 |
| 5 Dec 1998 | Premier League | A | Wimbledon | Wimbledon 1998–99 | 1–2 | Gary McAllister | 11,717 |
| 14 Dec 1998 | Premier League | A | Leeds United | Leeds United 1998–99 | 0–2 | 31,802 | |
| 19 Dec 1998 | Premier League | H | Derby County | Derby County 1998–99 | 1–1 | Noel Whelan | 16,627 |
| 26 Dec 1998 | Premier League | H | Tottenham Hotspur | Tottenham Hotspur 1998–99 | 1–1 | John Aloisi | 23,098 |
| 28 Dec 1998 | Premier League | A | West Ham United | West Ham United 1998–99 | 0–2 | 25,662 | |
| 2 Jan 1999 | FA Cup | H | Macclesfield Town | 7–0 | Steve Froggatt, Noel Whelan, Steve Payne, Darren Huckerby, Darren Huckerby, Darren Huckerby, George Boateng | 14,197 | |
| 9 Jan 1999 | Premier League | H | Nottingham Forest | Nottingham Forest 1998–99 | 4–0 | Darren Huckerby, Darren Huckerby, Darren Huckerby, Paul Telfer | 17,172 |
| 16 Jan 1999 | Premier League | A | Chelsea | Chelsea 1998–99 | 1–2 | Darren Huckerby | 34,869 |
| 23 Jan 1999 | FA Cup | A | Leicester City | Leicester City 1998–99 | 3–0 | Noel Whelan, Steve Froggatt, Paul Telfer | 21,207 |
| 30 Jan 1999 | Premier League | H | Liverpool | Liverpool 1998–99 | 2–1 | George Boateng, Noel Whelan | 23,056 |
| 6 Feb 1999 | Premier League | A | Tottenham Hotspur | Tottenham Hotspur 1998–99 | 0–0 | 34,376 | |
| 13 Feb 1999 | FA Cup | A | Everton | Everton 1998–99 | 1–2 | Gary McAllister | 33,907 |
| 17 Feb 1999 | Premier League | A | Newcastle United | Newcastle United 1998–99 | 1–4 | Noel Whelan | 36,352 |
| 20 Feb 1999 | Premier League | H | Manchester United | Manchester United 1998–99 | 0–1 | 22,596 | |
| 27 Feb 1999 | Premier League | A | Aston Villa | Aston Villa 1998–99 | 4–1 | John Aloisi, John Aloisi, George Boateng, George Boateng | 38,799 |
| 6 Mar 1999 | Premier League | H | Charlton Athletic | Charlton Athletic 1998–99 | 2–1 | Noel Whelan, Trond Egil Soltvedt | 20,259 |
| 13 Mar 1999 | Premier League | H | Blackburn Rovers | Blackburn Rovers 1998–99 | 1–1 | John Aloisi | 19,701 |
| 20 Mar 1999 | Premier League | A | Arsenal | Arsenal 1998–99 | 0–2 | 38,073 | |
| 3 Apr 1999 | Premier League | A | Sheffield Wednesday | Sheffield Wednesday 1998–99 | 2–1 | Gary McAllister, Noel Whelan | 28,136 |
| 5 Apr 1999 | Premier League | H | Southampton | Southampton 1998–99 | 1–0 | George Boateng | 21,402 |
| 11 Apr 1999 | Premier League | A | Everton | Everton 1998–99 | 0–2 | 32,341 | |
| 17 Apr 1999 | Premier League | H | Middlesbrough | Middlesbrough 1998–99 | 1–2 | Gary McAllister | 19,231 |
| 24 Apr 1999 | Premier League | A | Leicester City | Leicester City 1998–99 | 0–1 | 20,224 | |
| 1 May 1999 | Premier League | H | Wimbledon | Wimbledon 1998–99 | 2–1 | Darren Huckerby, Noel Whelan | 21,200 |
| 8 May 1999 | Premier League | A | Derby County | Derby County 1998–99 | 0–0 | 32,450 | |
| 16 May 1999 | Premier League | H | Leeds United | Leeds United 1998–99 | 2–2 | John Aloisi, Paul Telfer | 23,049 |
55 of the goals in this season carry a named scorer.
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