FA Cup   M. W D L goals
  at home 1 0 0 1 1 : 4
  Away 2 0 1 1 3 : 6
  3 0 1 2 4 : 10
League Cup   M. W D L goals
  at home 1 0 0 1 0 : 1
  1 0 0 1 0 : 1
overall   M. W D L goals
  at home 2 0 0 2 1 : 5
  Away 2 0 1 1 3 : 6
  Neutral Place 0 0 0 0 0 : 0
  4 0 1 3 4 : 11
FA Cup
2008/2009 3. Round Southend United - Chelsea FC 1:4 (1:1)
2008/2009 3. Round Chelsea FC - Southend United 1:1 (1:0)
1912/1913 1. Round Chelsea FC - Southend United 5:2
League Cup
1972/1973 2. Round Southend United - Chelsea FC 0:1

For games that were decided on penalties the score after 120 minutes will be included in the ranking