| Derby County FC v Coventry City FC 22/01/2000 | View match | |
| Coventry City FC v Charlton Athletic FC 29/01/2000 | View match | |
| Manchester United FC v Coventry City FC 05/02/2000 | View match | |
| Coventry City FC v Sunderland FC 12/02/2000 | View match | |
| Middlesbrough FC v Coventry City FC 19/02/2000 | View match | |
| Coventry City FC v Tottenham Hotspur FC 26/02/2000 | £4.50 | |
| Leeds United FC v Coventry City FC 05/03/2000 | View match | |
| Aston Villa FC v Coventry City FC 11/03/2000 | £4.50 | |
| Coventry City FC v Everton FC 15/03/2000 | View match | |
| Coventry City FC v Bradford City FC 18/03/2000 | View match | |
| Arsenal FC v Coventry City FC 26/03/2000 | £3.00 | |
| Coventry City FC v Liverpool FC 01/04/2000 | View match |