| 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 | |
| Bradford City FC v Coventry City FC 06/11/1999 | View match | |
| Coventry City FC v Aston Villa FC 22/11/1999 | View match | |
| Coventry City FC v Leicester City FC 27/11/1999 | View match | |
| Southampton FC v Coventry City FC 04/12/1999 | £3.50 | |
| Southampton FC v Coventry City FC 04/12/1999 | £3.50 | |
| Southampton FC v Coventry City FC 04/12/1999 | £4.50 | |
| Norwich City FC v Coventry City FC 11/12/1999 | View match | |
| Liverpool FC v Coventry City FC 18/12/1999 | View match | |
| Coventry City FC v Arsenal FC 26/12/1999 | View match |