Chelsea 4 - 0 Sunderland (Premiership: 07-08-1999)
Chelsea 3 - 0 Skonto Riga (European Cup: 11-08-1999)
Leicester 2 - 2 Chelsea (Premiership: 14-08-1999)
Chelsea 1 - 0 Aston Villa (Premiership: 21-08-1999)
Skonto Riga 0 - 0 Chelsea (European Cup: 25-08-1999)
Wimbledon 0 - 1 Chelsea (Premiership: 28-08-1999)
Chelsea 1 - 0 Newcastle (Premiership: 11-09-1999)
Chelsea 0 - 0 Milan (European Cup: 15-09-1999)
Watford 1 - 0 Chelsea (Premiership: 18-09-1999)
Hertha Berlin 2 - 1 Chelsea (European Cup: 21-09-1999)
Middlesbrough 0 - 1 Chelsea (Premiership: 25-09-1999)
Chelsea 1 - 0 Galatasaray (European Cup: 28-09-1999)
Chelsea 5 - 0 Man Utd (Premiership: 03-10-1999)
Chelsea 0 - 1 Huddersfield (League Cup: 13-10-1999)
Liverpool 1 - 0 Chelsea (Premiership: 16-10-1999)
Galatasaray 0 - 5 Chelsea (European Cup: 20-10-1999)
Chelsea 2 - 3 Arsenal (Premiership: 23-10-1999)
Milan 1 - 1 Chelsea (European Cup: 26-10-1999)
Derby 3 - 1 Chelsea (Premiership: 30-10-1999)
Chelsea 2 - 0 Hertha Berlin (European Cup: 03-11-1999)
Chelsea 0 - 0 West Ham (Premiership: 07-11-1999)
Everton 1 - 1 Chelsea (Premiership: 20-11-1999)
Chelsea 3 - 1 Feyenoord (European Cup: 24-11-1999)
Chelsea 1 - 0 Bradford (Premiership: 28-11-1999)
Sunderland 4 - 1 Chelsea (Premiership: 04-12-1999)
Lazio 0 - 0 Chelsea (European Cup: 07-12-1999)
Hull City 1 - 6 Chelsea (FA Cup: 11-12-1999)
Chelsea 0 - 2 Leeds (Premiership: 19-12-1999)
Southampton 1 - 2 Chelsea (Premiership: 26-12-1999)
Chelsea 3 - 0 Sheff Wed (Premiership: 29-12-1999)
Coventry 2 - 2 Chelsea (Premiership: 04-01-2000)
Bradford 1 - 1 Chelsea (Premiership: 08-01-2000)
Chelsea 1 - 0 Tottenham (Premiership: 12-01-2000)
Chelsea 1 - 1 Leicester (Premiership: 15-01-2000)
Chelsea 2 - 0 Nottingham Forest (FA Cup: 19-01-2000)
Aston Villa 0 - 0 Chelsea (Premiership: 22-01-2000)
Chelsea 2 - 1 Leicester (FA Cup: 30-01-2000)
Tottenham 0 - 1 Chelsea (Premiership: 05-02-2000)
Chelsea 3 - 1 Wimbledon (Premiership: 12-02-2000)
Chelsea 5 - 0 Gillingham (FA Cup: 20-02-2000)
Chelsea 2 - 1 Watford (Premiership: 26-02-2000)
Marseille 1 - 0 Chelsea (European Cup: 29-02-2000)
Newcastle 0 - 1 Chelsea (Premiership: 04-03-2000)
Chelsea 1 - 0 Marseille (European Cup: 08-03-2000)
Chelsea 1 - 1 Everton (Premiership: 11-03-2000)
Feyenoord 1 - 3 Chelsea (European Cup: 14-03-2000)
West Ham 0 - 0 Chelsea (Premiership: 18-03-2000)
Chelsea 1 - 2 Lazio (European Cup: 22-03-2000)
Chelsea 1 - 1 Southampton (Premiership: 25-03-2000)
Leeds 0 - 1 Chelsea (Premiership: 01-04-2000)
Chelsea 3 - 1 Barcelona (European Cup: 05-04-2000)
Newcastle 1 - 2 Chelsea (FA Cup: 09-04-2000)
Chelsea 2 - 1 Coventry (Premiership: 12-04-2000)
Sheff Wed 1 - 0 Chelsea (Premiership: 15-04-2000)
Barcelona 5 - 1 Chelsea (European Cup: 18-04-2000)
Chelsea 1 - 1 Middlesbrough (Premiership: 22-04-2000)
Man Utd 3 - 2 Chelsea (Premiership: 24-04-2000)
Chelsea 2 - 0 Liverpool (Premiership: 29-04-2000)
Arsenal 2 - 1 Chelsea (Premiership: 06-05-2000)
Chelsea 4 - 0 Derby (Premiership: 14-05-2000)
Aston Villa 0 - 1 Chelsea (FA Cup: 20-05-2000)
