| Coventry City FC v Manchester United FC 25/08/1999 | View match | |
| Sunderland FC v Coventry City FC 29/08/1999 | View match | |
| Coventry City FC v Leeds United FC 11/09/1999 | View match | |
| Tranmere Rovers FC v Coventry City FC 14/09/1999 | View match | |
| Tottenham Hotspur FC v Coventry City FC 19/09/1999 | £4.00 | |
| Tottenham Hotspur FC v Coventry City FC 19/09/1999 | £5.00 | |
| Coventry City FC v Tranmere Rovers FC 22/09/1999 | View match | |
| Coventry City FC v West Ham United FC 25/09/1999 | View match | |
| Everton FC v Coventry City FC 02/10/1999 | View match | |
| Coventry City FC v Newcastle United FC 16/10/1999 | View match | |
| Sheffield Wednesday FC v Coventry City FC 23/10/1999 | £4.00 | |
| Coventry City FC v Watford FC 31/10/1999 | View match |