28th May 1988

Final 2nd Leg Chelsea 1-0 Middlesbrough

25th May 1988

Final 1st Leg Middlesbrough 2-0 Chelsea

18th May 1988

Semi Final 2nd Leg Middlesbrough 2-0 Bradford City
Semi Final 2nd Leg Chelsea 4-1 Blackburn Rovers

15th May 1988

Semi Final 1st Leg Bradford City 2-1 Middlesbrough
Semi Final 1st Leg Blackburn Rovers 0-2 Chelsea