Every competitive match Coventry City played in 1999–00, 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 |
|---|---|---|---|---|---|---|---|
| 7 Aug 1999 | Premier League | H | Southampton | Southampton 1999–00 | 0–1 | 19,915 | |
| 11 Aug 1999 | Premier League | A | Leicester City | Leicester City 1999–00 | 0–1 | 19,196 | |
| 14 Aug 1999 | Premier League | A | Wimbledon | Wimbledon 1999–00 | 1–1 | Gary McAllister | 10,635 |
| 21 Aug 1999 | Premier League | H | Derby County | Derby County 1999–00 | 2–0 | Robbie Keane, Robbie Keane | 17,685 |
| 25 Aug 1999 | Premier League | H | Manchester United | Manchester United 1999–00 | 1–2 | John Aloisi | 22,024 |
| 29 Aug 1999 | Premier League | A | Sunderland | Sunderland 1999–00 | 1–1 | Keane | 39,427 |
| 11 Sep 1999 | Premier League | H | Leeds United | Leeds United 1999–00 | 3–4 | Gary McAllister, Aloisi, Youssef Chippo | 21,532 |
| 14 Sep 1999 | League Cup | A | Tranmere Rovers | Tranmere Rovers 1999–00 | 1–5 | Gary McAllister | 6,759 |
| 19 Sep 1999 | Premier League | A | Tottenham Hotspur | Tottenham Hotspur 1999–00 | 2–3 | Keane, Youssef Chippo | 35,224 |
| 22 Sep 1999 | League Cup | H | Tranmere Rovers | Tranmere Rovers 1999–00 | 3–1 | Gary McAllister, Youssef Chippo, Youssef Chippo | 12,433 |
| 25 Sep 1999 | Premier League | H | West Ham United | West Ham United 1999–00 | 1–0 | Moustapha Hadji | 19,993 |
| 2 Oct 1999 | Premier League | A | Everton | Everton 1999–00 | 1–1 | Gary McAllister | 34,839 |
| 16 Oct 1999 | Premier League | H | Newcastle United | Newcastle United 1999–00 | 4–1 | Carlton Palmer, Paul Williams, Keane, Hadji | 23,031 |
| 23 Oct 1999 | Premier League | A | Sheffield Wednesday | Sheffield Wednesday 1999–00 | 0–0 | 23,296 | |
| 31 Oct 1999 | Premier League | H | Watford | Watford 1999–00 | 4–0 | Keane, Steve Froggatt, Hadji, Gary McAllister | 21,700 |
| 6 Nov 1999 | Premier League | A | Bradford City | Bradford City 1999–00 | 1–1 | Gary McAllister | 17,587 |
| 22 Nov 1999 | Premier League | H | Aston Villa | Aston Villa 1999–00 | 2–1 | Cedric Roussel, Keane | 20,184 |
| 27 Nov 1999 | Premier League | H | Leicester City | Leicester City 1999–00 | 0–1 | 22,021 | |
| 4 Dec 1999 | Premier League | A | Southampton | Southampton 1999–00 | 0–0 | 15,168 | |
| 11 Dec 1999 | FA Cup | A | Norwich City | Norwich City 1999–00 | 3–1 | Noel Whelan, Cedric Roussel, John Eustace | 15,702 |
| 18 Dec 1999 | Premier League | A | Liverpool | Liverpool 1999–00 | 0–2 | 44,024 | |
| 26 Dec 1999 | Premier League | H | Arsenal | Arsenal 1999–00 | 3–2 | Gary McAllister, Hadji, Keane | 22,757 |
| 4 Jan 2000 | Premier League | H | Chelsea | Chelsea 1999–00 | 2–2 | Roussel, Keane | 20,164 |
| 8 Jan 2000 | FA Cup | H | Burnley | Burnley 1999–00 | 3–0 | Youssef Chippo, Youssef Chippo, Noel Whelan | 22,774 |
| 15 Jan 2000 | Premier League | H | Wimbledon | Wimbledon 1999–00 | 2–0 | Gary McAllister, Keane | 19,012 |
| 22 Jan 2000 | Premier League | A | Derby County | Derby County 1999–00 | 0–0 | 28,381 | |
| 29 Jan 2000 | FA Cup | H | Charlton Athletic | Charlton Athletic 1999–00 | 2–3 | Roussel, Roussel | 23,400 |
| 5 Feb 2000 | Premier League | A | Manchester United | Manchester United 1999–00 | 2–3 | Roussel, Roussel | 61,380 |
| 12 Feb 2000 | Premier League | H | Sunderland | Sunderland 1999–00 | 3–2 | Keane, Hadji, Roussel | 22,101 |
| 19 Feb 2000 | Premier League | A | Middlesbrough | Middlesbrough 1999–00 | 0–2 | 32,798 | |
| 26 Feb 2000 | Premier League | H | Tottenham Hotspur | Tottenham Hotspur 1999–00 | 0–1 | 23,077 | |
| 5 Mar 2000 | Premier League | A | Leeds United | Leeds United 1999–00 | 0–3 | 38,710 | |
| 11 Mar 2000 | Premier League | A | Aston Villa | Aston Villa 1999–00 | 0–1 | 33,177 | |
| 15 Mar 2000 | Premier League | H | Everton | Everton 1999–00 | 1–0 | Gary McAllister | 18,518 |
| 18 Mar 2000 | Premier League | H | Bradford City | Bradford City 1999–00 | 4–0 | Roussel, Noel Whelan, John Eustace, Ysrael Zúñiga | 19,201 |
| 26 Mar 2000 | Premier League | A | Arsenal | Arsenal 1999–00 | 0–3 | 38,027 | |
| 1 Apr 2000 | Premier League | H | Liverpool | Liverpool 1999–00 | 0–3 | 23,098 | |
| 12 Apr 2000 | Premier League | A | Chelsea | Chelsea 1999–00 | 1–2 | Gary McAllister | 32,316 |
| 15 Apr 2000 | Premier League | H | Middlesbrough | Middlesbrough 1999–00 | 2–1 | Paul Ince, Keane | 19,435 |
| 22 Apr 2000 | Premier League | A | West Ham United | West Ham United 1999–00 | 0–5 | 24,719 | |
| 29 Apr 2000 | Premier League | A | Newcastle United | Newcastle United 1999–00 | 0–2 | 36,408 | |
| 6 May 2000 | Premier League | H | Sheffield Wednesday | Sheffield Wednesday 1999–00 | 4–1 | Gary McAllister, Gary McAllister, Zúñiga, Hadji | 19,921 |
| 14 May 2000 | Premier League | A | Watford | Watford 1999–00 | 0–1 | 18,977 |
59 of the goals in this season carry a named scorer.
All 107 Coventry City seasons · Coventry City head-to-head records · Coventry City players