| League | Date | Home Team | Score | Away Team |
|---|---|---|---|---|
| PL | 16-05-1999 | Chelsea | 2 - 1 | Derby |
| PL | 10-05-1999 | Tottenham | 2 - 2 | Chelsea |
| PL | 05-05-1999 | Chelsea | 1 - 0 | Leeds |
| PL | 01-05-1999 | Chelsea | 3 - 1 | Everton |
| PL | 25-04-1999 | Sheffield Weds | 0 - 0 | Chelsea |
| PL | 18-04-1999 | Chelsea | 2 - 2 | Leicester |
| PL | 14-04-1999 | Middlesbrough | 0 - 0 | Chelsea |
| PL | 11-04-1999 | Wimbledon | 1 - 2 | Chelsea |
| PL | 03-04-1999 | Charlton | 0 - 1 | Chelsea |
| PL | 21-03-1999 | Aston Villa | 0 - 3 | Chelsea |
| PL | 13-03-1999 | Chelsea | 0 - 1 | West Ham |
| PL | 27-02-1999 | Chelsea | 2 - 1 | Liverpool |
| PL | 20-02-1999 | Notts Forest | 1 - 3 | Chelsea |
| PL | 17-02-1999 | Chelsea | 1 - 1 | Blackburn |
| PL | 06-02-1999 | Chelsea | 1 - 0 | Southampton |
| PL | 31-01-1999 | Arsenal | 1 - 0 | Chelsea |
| PL | 16-01-1999 | Chelsea | 2 - 1 | Coventry |
| PL | 09-01-1999 | Newcastle | 0 - 1 | Chelsea |
| PL | 29-12-1998 | Chelsea | 0 - 0 | Man United |
| PL | 26-12-1998 | Southampton | 0 - 2 | Chelsea |
| PL | 19-12-1998 | Chelsea | 2 - 0 | Tottenham |
| PL | 16-12-1998 | Man United | 1 - 1 | Chelsea |
| PL | 12-12-1998 | Derby | 2 - 2 | Chelsea |
| PL | 09-12-1998 | Chelsea | 2 - 1 | Aston Villa |
| PL | 05-12-1998 | Everton | 0 - 0 | Chelsea |
| PL | 28-11-1998 | Chelsea | 1 - 1 | Sheffield Weds |
| PL | 21-11-1998 | Leicester | 2 - 4 | Chelsea |
| PL | 14-11-1998 | Chelsea | 3 - 0 | Wimbledon |
| PL | 08-11-1998 | West Ham | 1 - 1 | Chelsea |
| PL | 25-10-1998 | Leeds | 0 - 0 | Chelsea |
| PL | 17-10-1998 | Chelsea | 2 - 1 | Charlton |
| PL | 04-10-1998 | Liverpool | 1 - 1 | Chelsea |
| PL | 26-09-1998 | Chelsea | 2 - 0 | Middlesbrough |
| PL | 21-09-1998 | Blackburn | 3 - 4 | Chelsea |
| PL | 12-09-1998 | Chelsea | 2 - 1 | Notts Forest |
| PL | 09-09-1998 | Chelsea | 0 - 0 | Arsenal |
| PL | 22-08-1998 | Chelsea | 1 - 1 | Newcastle |
| PL | 15-08-1998 | Coventry | 2 - 1 | Chelsea |