CHELSEA    1965/66
      Fairs Cup
     
   

Chelsea qualified for the Fairs Cup by League position, finishing third in the First Division in 1964/65.

   
1st Round 
1st Leg Wed Sep 22 AS Roma (Italy) Home Won 4-1
2nd Leg Wed Oct 6 AS Roma Away Drew 0-0
Won 4-1 on aggregate.
2nd Round 
1st Leg Wed Nov 17 Vienna Sport Club (Austria) Away Lost 0-1
2nd Leg Wed Dec 1 Vienna Sport Club Home Won 2-0
Won 2-1 on aggregate.
3rd Round 
1st Leg Wed Feb 9 AC Milan (Italy) Away Lost 1-2
2nd Leg Wed Feb 16 AC Milan Home Won 2-1
Replay Wed Mar 2 AC Milan Away Drew 1-1

After finishing the two legs all-square at 3-3 Chelsea lost the toss of a coin to decide the venue for the play-off. The decider in Milan also ended all-square and this time Chelsea captain Ron Harris made the right choice with a toss of the coin deciding that Chelsea would progress.

4th Round 
1st Leg Tue Mar 15 Munich 1860 (West Germany) Away Drew 2-2
2nd Leg Tue Mar 29 Munich 1860 Home Won 1-0
Won 3-2 on aggregate.
Semi-Final 
1st Leg Wed Apr 27 Barcelona (Spain) Away Lost 0-2
2nd Leg Wed May 11 Barcelona Home Won 2-0
Play Off Wed May 25 Barcelona Away Lost 0-5

It proved to be another tie that needed a third match to decide. Chelsea again lost the toss of the coin to decide venue with Barcelona then making home advantage pay to the full.