FA Cup   M. W D L goals
  at home 4 1 2 1 6 : 6
  Away 3 1 0 2 5 : 7
  7 2 2 3 11 : 13
League One   M. W D L goals
  at home 3 1 0 2 6 : 8
  Away 3 1 1 1 1 : 1
  6 2 1 3 7 : 9
League Two   M. W D L goals
  at home 4 2 1 1 5 : 4
  Away 4 1 0 3 5 : 11
  8 3 1 4 10 : 15
National League   M. W D L goals
  at home 3 2 1 0 8 : 4
  Away 3 2 0 1 7 : 3
  6 4 1 1 15 : 7
overall   M. W D L goals
  at home 14 6 4 4 25 : 22
  Away 13 5 1 7 18 : 22
  Neutral Place 0 0 0 0 0 : 0
  27 11 5 11 43 : 44
FA Cup
2021/2022 1. Round Chesterfield FC - Southend United 3:1 (2:1)
2013/2014 2. Round Chesterfield FC - Southend United 1:3 (1:2)
2001/2002 2. Round Southend United - Chesterfield FC 2:0 (1:0)
2001/2002 2. Round Chesterfield FC - Southend United 1:1 (0:0)
1953/1954 2. Round Southend United - Chesterfield FC 1:2
1938/1939 3. Round Southend United - Chesterfield FC 4:3
1938/1939 3. Round Chesterfield FC - Southend United 1:1
League One
2016/2017 43. Round Chesterfield FC - Southend United 0:4 (0:1)
2016/2017 13. Round Southend United - Chesterfield FC 1:0 (1:0)
2015/2016 35. Round Southend United - Chesterfield FC 0:1 (0:0)
2015/2016 14. Round Chesterfield FC - Southend United 3:0 (2:0)
2005/2006 34. Round Chesterfield FC - Southend United 3:4 (1:0)
2005/2006 20. Round Southend United - Chesterfield FC 0:0 (0:0)
League Two
2013/2014 27. Round Southend United - Chesterfield FC 3:0 (1:0)
2013/2014 4. Round Chesterfield FC - Southend United 2:1 (0:0)
2012/2013 30. Round Chesterfield FC - Southend United 0:1 (0:0)
2012/2013 23. Round Southend United - Chesterfield FC 3:0 (0:0)
2010/2011 26. Round Southend United - Chesterfield FC 2:3 (0:2)
2010/2011 11. Round Chesterfield FC - Southend United 2:1 (1:1)
2000/2001 40. Round Chesterfield FC - Southend United 1:1
2000/2001 21. Round Southend United - Chesterfield FC 3:2
National League
2023/2024 31. Round Chesterfield FC - Southend United 3:0 (1:0)
2023/2024 20. Round Southend United - Chesterfield FC 2:1 (0:1)
2022/2023 37. Round Southend United - Chesterfield FC 1:2 (0:1)
2022/2023 9. Round Chesterfield FC - Southend United 3:2 (1:1)
2021/2022 33. Round Chesterfield FC - Southend United 2:2 (1:0)
2021/2022 11. Round Southend United - Chesterfield FC 0:4 (0:2)

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