| Tottenham Hotspur FC v Coventry City FC 06/02/1999 | £2.00 | |
| Aston Villa FC v Coventry City FC 27/02/1999 | £3.50 | |
| Arsenal FC v Coventry City FC 20/03/1999 | £3.50 | |
| Arsenal FC v Coventry City FC 20/03/1999 | £2.50 | |
| Arsenal FC v Coventry City FC 20/03/1999 | £4.00 | |
| Arsenal FC v Coventry City FC 20/03/1999 | £3.50 | |
| Arsenal FC v Coventry City FC 20/03/1999 | £3.00 | |
| Tottenham Hotspur FC v Coventry City FC 19/09/1999 | £4.00 | |
| Tottenham Hotspur FC v Coventry City FC 19/09/1999 | £5.00 | |
| Sheffield Wednesday FC v Coventry City FC 23/10/1999 | £4.00 | |
| Southampton FC v Coventry City FC 04/12/1999 | £3.50 | |
| Southampton FC v Coventry City FC 04/12/1999 | £3.50 |