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Chelsea qualified for the Champions League by finishing third in the Premier Division in 1998/99.
   
3rd Qualifying Round
1st Leg Wed Aug 11 Skonto Riga (Latvia) Home Won 3-0
2nd Leg Wed Aug 25 Skonto Riga Away Drew 0-0
Won 3-0 on aggregate.
Champions League First Group Stage
Group H Wed Sep 15 AC Milan (Italy) Home Drew 0-0
Group H Tue Sep 21 Hertha Berlin (Germany) Away Lost 1-2
Group H Tue Sep 28 Galatasaray (Turkey) Home Won 1-0
Group H Wed Oct 20 Galatasaray Away Won 5-0
Group H Tue Oct 26 AC Milan Away Drew 1-1
Group H Wed Nov 3 Hertha Berlin Home Won 2-0
Chelsea won the Group and qualified for the Second Group Stage. Full Group results and table.
Champions League Second Group Stage
Group D Wed Nov 24 Feyenoord (Holland) Home Won 3-1
Group D Tue Dec 7 Lazio (Italy) Away Drew 0-0
Group D Tue Feb 29 Marseille (France) Away Lost 0-1
Group D Wed Mar 8 Marseille  Home Won 1-0
Group D Tue Mar 14 Feyenoord Away Won 3-1
Group D Wed Mar 22 Lazio Home Lost 1-2
Chelsea finished second in the Group and qualified for the Quarter Finals. Full Group results and table.
Quarter Final
1st Leg Wed Apr 5 Barcelona (Spain) Home Won 3-1
2nd Leg Tue Apr 18 Barcelona Away Lost 1-5
Lost 4-6 on aggregate.