| League | Date | Home Team | Score | Away Team |
|---|---|---|---|---|
| PL | 16-05-1999 | Coventry | 2 - 2 | Leeds |
| PL | 08-05-1999 | Derby | 0 - 0 | Coventry |
| PL | 01-05-1999 | Coventry | 2 - 1 | Wimbledon |
| PL | 24-04-1999 | Leicester | 1 - 0 | Coventry |
| PL | 17-04-1999 | Coventry | 1 - 2 | Middlesbrough |
| PL | 11-04-1999 | Everton | 2 - 0 | Coventry |
| PL | 05-04-1999 | Coventry | 1 - 0 | Southampton |
| PL | 03-04-1999 | Sheffield Weds | 1 - 2 | Coventry |
| PL | 20-03-1999 | Arsenal | 2 - 0 | Coventry |
| PL | 13-03-1999 | Coventry | 1 - 1 | Blackburn |
| PL | 06-03-1999 | Coventry | 2 - 1 | Charlton |
| PL | 27-02-1999 | Aston Villa | 1 - 4 | Coventry |
| PL | 20-02-1999 | Coventry | 0 - 1 | Man United |
| PL | 17-02-1999 | Newcastle | 4 - 1 | Coventry |
| PL | 06-02-1999 | Tottenham | 0 - 0 | Coventry |
| PL | 30-01-1999 | Coventry | 2 - 1 | Liverpool |
| PL | 16-01-1999 | Chelsea | 2 - 1 | Coventry |
| PL | 09-01-1999 | Coventry | 4 - 0 | Notts Forest |
| PL | 28-12-1998 | West Ham | 2 - 0 | Coventry |
| PL | 26-12-1998 | Coventry | 1 - 1 | Tottenham |
| PL | 19-12-1998 | Coventry | 1 - 1 | Derby |
| PL | 14-12-1998 | Leeds | 2 - 0 | Coventry |
| PL | 05-12-1998 | Wimbledon | 2 - 1 | Coventry |
| PL | 28-11-1998 | Coventry | 1 - 1 | Leicester |
| PL | 21-11-1998 | Middlesbrough | 2 - 0 | Coventry |
| PL | 15-11-1998 | Coventry | 3 - 0 | Everton |
| PL | 07-11-1998 | Blackburn | 1 - 2 | Coventry |
| PL | 31-10-1998 | Coventry | 0 - 1 | Arsenal |
| PL | 24-10-1998 | Southampton | 2 - 1 | Coventry |
| PL | 18-10-1998 | Coventry | 1 - 0 | Sheffield Weds |
| PL | 03-10-1998 | Coventry | 1 - 2 | Aston Villa |
| PL | 26-09-1998 | Charlton | 1 - 1 | Coventry |
| PL | 19-09-1998 | Coventry | 1 - 5 | Newcastle |
| PL | 12-09-1998 | Man United | 2 - 0 | Coventry |
| PL | 09-09-1998 | Liverpool | 2 - 0 | Coventry |
| PL | 29-08-1998 | Coventry | 0 - 0 | West Ham |
| PL | 22-08-1998 | Notts Forest | 1 - 0 | Coventry |
| PL | 15-08-1998 | Coventry | 2 - 1 | Chelsea |