| League | Date | Home Team | Score | Away Team |
|---|---|---|---|---|
| PL | 14-05-2000 | Watford | 1 - 0 | Coventry |
| PL | 06-05-2000 | Coventry | 4 - 1 | Sheffield Weds |
| PL | 29-04-2000 | Newcastle | 2 - 0 | Coventry |
| PL | 22-04-2000 | West Ham | 5 - 0 | Coventry |
| PL | 15-04-2000 | Coventry | 2 - 1 | Middlesbrough |
| PL | 12-04-2000 | Chelsea | 2 - 1 | Coventry |
| PL | 01-04-2000 | Coventry | 0 - 3 | Liverpool |
| PL | 26-03-2000 | Arsenal | 3 - 0 | Coventry |
| PL | 18-03-2000 | Coventry | 4 - 0 | Bradford |
| PL | 15-03-2000 | Coventry | 1 - 0 | Everton |
| PL | 11-03-2000 | Aston Villa | 1 - 0 | Coventry |
| PL | 05-03-2000 | Leeds | 3 - 0 | Coventry |
| PL | 26-02-2000 | Coventry | 0 - 1 | Tottenham |
| PL | 19-02-2000 | Middlesbrough | 2 - 0 | Coventry |
| PL | 12-02-2000 | Coventry | 3 - 2 | Sunderland |
| PL | 05-02-2000 | Man United | 3 - 2 | Coventry |
| PL | 22-01-2000 | Derby | 0 - 0 | Coventry |
| PL | 15-01-2000 | Coventry | 2 - 0 | Wimbledon |
| PL | 04-01-2000 | Coventry | 2 - 2 | Chelsea |
| PL | 26-12-1999 | Coventry | 3 - 2 | Arsenal |
| PL | 18-12-1999 | Liverpool | 2 - 0 | Coventry |
| PL | 04-12-1999 | Southampton | 0 - 0 | Coventry |
| PL | 27-11-1999 | Coventry | 0 - 1 | Leicester |
| PL | 22-11-1999 | Coventry | 2 - 1 | Aston Villa |
| PL | 06-11-1999 | Bradford | 1 - 1 | Coventry |
| PL | 31-10-1999 | Coventry | 4 - 0 | Watford |
| PL | 23-10-1999 | Sheffield Weds | 0 - 0 | Coventry |
| PL | 16-10-1999 | Coventry | 4 - 1 | Newcastle |
| PL | 02-10-1999 | Everton | 1 - 1 | Coventry |
| PL | 25-09-1999 | Coventry | 1 - 0 | West Ham |
| PL | 19-09-1999 | Tottenham | 3 - 2 | Coventry |
| PL | 11-09-1999 | Coventry | 3 - 4 | Leeds |
| PL | 29-08-1999 | Sunderland | 1 - 1 | Coventry |
| PL | 25-08-1999 | Coventry | 1 - 2 | Man United |
| PL | 21-08-1999 | Coventry | 2 - 0 | Derby |
| PL | 14-08-1999 | Wimbledon | 1 - 1 | Coventry |
| PL | 11-08-1999 | Leicester | 1 - 0 | Coventry |
| PL | 07-08-1999 | Coventry | 0 - 1 | Southampton |