League Cup   M. W D L goals
  at home 1 0 0 1 1 : 2
  Away 2 1 0 1 2 : 4
  3 1 0 2 3 : 6
League One   M. W D L goals
  at home 2 0 2 0 1 : 1
  Away 2 0 1 1 2 : 4
  4 0 3 1 3 : 5
League Two   M. W D L goals
  at home 11 4 2 5 12 : 15
  Away 11 6 1 4 12 : 13
  22 10 3 9 24 : 28
overall   M. W D L goals
  at home 14 4 4 6 14 : 18
  Away 15 7 2 6 16 : 21
  Neutral Place 0 0 0 0 0 : 0
  29 11 6 12 30 : 39
League Cup
2009/2010 1. Round Cheltenham Town - Southend United 1:2 (1:0)
2008/2009 1. Round Southend United - Cheltenham Town 0:1 (0:0, 0:0) aet
2007/2008 1. Round Southend United - Cheltenham Town 4:1 (1:0, 1:1) aet
League One
2008/2009 46. Round Southend United - Cheltenham Town 2:0 (0:0)
2008/2009 18. Round Cheltenham Town - Southend United 0:0 (0:0)
2007/2008 35. Round Cheltenham Town - Southend United 1:1 (1:0)
2007/2008 16. Round Southend United - Cheltenham Town 2:2 (0:2)
League Two
2020/2021 33. Round Cheltenham Town - Southend United 1:0 (0:0)
2020/2021 6. Round Southend United - Cheltenham Town 0:2 (0:1)
2014/2015 30. Round Southend United - Cheltenham Town 2:0 (2:0)
2014/2015 8. Round Cheltenham Town - Southend United 0:1 (0:0)
2013/2014 41. Round Cheltenham Town - Southend United 1:2 (1:0)
2013/2014 19. Round Southend United - Cheltenham Town 1:1 (1:0)
2012/2013 27. Round Southend United - Cheltenham Town 1:2 (0:2)
2012/2013 6. Round Cheltenham Town - Southend United 1:3 (1:1)
2011/2012 40. Round Southend United - Cheltenham Town 4:0 (2:0)
2011/2012 20. Round Cheltenham Town - Southend United 3:0 (1:0)
2010/2011 25. Round Southend United - Cheltenham Town 1:2 (0:2)
2010/2011 15. Round Cheltenham Town - Southend United 0:2 (0:2)
2004/2005 38. Round Cheltenham Town - Southend United 0:3 (0:2)
2004/2005 1. Round Southend United - Cheltenham Town 0:2 (0:2)
2003/2004 26. Round Cheltenham Town - Southend United 1:1
2003/2004 1. Round Southend United - Cheltenham Town 2:0
2001/2002 32. Round Cheltenham Town - Southend United 1:1
2001/2002 11. Round Southend United - Cheltenham Town 0:1
2000/2001 46. Round Cheltenham Town - Southend United 2:1
2000/2001 19. Round Southend United - Cheltenham Town 0:1
1999/2000 46. Round Southend United - Cheltenham Town 2:1
1999/2000 11. Round Cheltenham Town - Southend United 2:1

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