Click the score to see the report..
| Chelsea | 2 - 1 | Derby | Premiership | 16th May 1999 |
| Chelsea | 3 - 1 | Everton | Premiership | 1st May 1999 |
| Chelsea | 0 - 1 | West Ham | Premiership | 13th March 1999 |
| Chelsea | 3 - 0 | Vålerenga | ECWC (¼) 1st leg | 4th March 1999 |
| Chelsea | 2 - 1 | Liverpool | Premiership | 27th February 1999 |
| Chelsea | 1 - 0 | Southampton | Premiership | 6th February 1999 |
| Chelsea | 4 - 2 | Oxford | FA Cup 4th rnd replay | 3rd February 1999 |
| Bumnal | 1 - 0 | Chelsea | Premiership | 31st January 1999 |
| Chelsea | 2 - 0 | Rottenham | Premiership | 19th December 1998 |
| Chelsea | 2 - 1 | Aston Villa | Premiership | 9th December 1998 |
| Chelsea | 1 - 1 | Sheff Wed | Premiership | 28th November 1998 |
| Chelsea | 3 - 0 | Wimbledon | Premiership | 14th November 1998 |
| Bumnal | 0 - 5 | Chelsea | Worthington Cup (4) | 11th November 1998 |
| Chelsea | 1 - 1 | FC Copenhagen | ECWC (2) 1st leg | 22nd October 1998 |
| Chelsea | 2 - 1 | Charlton | Premiership | 17th October 1998 |
| Chelsea | 2 - 0 | Middlesbrough | Premiership | 26th September 1998 |
| Chelsea | 1 - 0 | Helsingborgs | ECWC (1) 1st leg | 17th September 1998 |
| Chelsea | 2 - 1 | Forest | Premiership | 12th September 1998 |
| Chelsea | 0 - 0 | Arsenal | Premiership | 8th September 1998 |
| Chelsea | 1 - 0 | Real Madrid | Super Cup | 28th August 1998 |
| Chelsea | 1 - 1 | Newcastle | Premiership | 22nd August 1998 |
