| Wimbledon v Chelsea FC 11/04/1999 | £4.50 | |
| Middlesbrough FC v Chelsea FC 14/04/1999 | £3.50 | |
| Chelsea FC v Leicester City FC 18/04/1999 | £3.50 | |
| Chelsea FC v Leicester City FC 18/04/1999 | £4.00 | |
| Real Mallorca/RCD Mallorca v Chelsea FC 22/04/1999 | £15.00 | |
| Chelsea FC v Everton FC 01/05/1999 | £2.50 | |
| Chelsea FC v Everton FC 01/05/1999 | £3.00 | |
| Chelsea FC v Everton FC 01/05/1999 | £3.50 | |
| Chelsea FC v Leeds United FC 05/05/1999 | £3.50 | |
| Chelsea FC v Leeds United FC 05/05/1999 | £3.00 | |
| Tottenham Hotspur FC v Chelsea FC 10/05/1999 | £2.50 | |
| Tottenham Hotspur FC v Chelsea FC 10/05/1999 | £4.50 |