| Arsenal FC v Coventry City FC 20/03/1999 | £3.50 | |
| Coventry City FC v Southampton FC 05/04/1999 | £5.00 | |
| Coventry City FC v Southampton FC 07/08/1999 | £3.50 | |
| Tottenham Hotspur FC v Coventry City FC 19/09/1999 | £5.00 | |
| Tottenham Hotspur FC v Coventry City FC 19/09/1999 | £4.00 | |
| Coventry City FC v West Ham United FC 25/09/1999 | £5.00 | |
| Sheffield Wednesday FC v Coventry City FC 23/10/1999 | £4.00 | |
| Southampton FC v Coventry City FC 04/12/1999 | £4.50 | |
| Southampton FC v Coventry City FC 04/12/1999 | £3.50 | |
| Southampton FC v Coventry City FC 04/12/1999 | £3.50 | |
| Coventry City FC v Chelsea FC 04/01/2000 | £3.50 | |
| Coventry City FC v Tottenham Hotspur FC 26/02/2000 | £4.50 |