| Arsenal FC v Coventry City FC 20/03/1999 | £3.50 | |
| Sheffield Wednesday FC v Coventry City FC 03/04/1999 | View match | |
| Coventry City FC v Southampton FC 05/04/1999 | £5.00 | |
| Everton FC v Coventry City FC 11/04/1999 | View match | |
| Coventry City FC v Middlesbrough FC 17/04/1999 | View match | |
| Leicester City FC v Coventry City FC 24/04/1999 | View match | |
| Coventry City FC v Wimbledon 01/05/1999 | View match | |
| Derby County FC v Coventry City FC 08/05/1999 | View match | |
| Coventry City FC v Leeds United FC 16/05/1999 | View match | |
| Coventry City FC v Southampton FC 07/08/1999 | £3.50 | |
| Leicester City FC v Coventry City FC 11/08/1999 | View match | |
| Wimbledon v Coventry City FC 14/08/1999 | View match |