Championship   M. W D L goals
  at home 3 2 0 1 9 : 2
  Away 3 1 1 1 4 : 9
  6 3 1 2 13 : 11
FA Cup   M. W D L goals
  at home 3 3 0 0 10 : 4
  Away 2 0 1 1 3 : 4
  Neutral Place 2 1 1 0 6 : 3
  7 4 2 1 19 : 11
League Cup   M. W D L goals
  at home 2 1 0 1 2 : 2
  Away 3 1 1 0 2 : 1
  5 2 1 1 4 : 3
overall   M. W D L goals
  at home 8 6 0 2 21 : 8
  Away 8 2 3 2 9 : 14
  Neutral Place 2 1 1 0 6 : 3
  18 9 4 4 36 : 25
Championship
1901/1902 7. Round Middlesbrough FC - Chesterfield FC 7:1
1901/1902 3. Round Chesterfield FC - Middlesbrough FC 0:0
1900/1901 5. Round Middlesbrough FC - Chesterfield FC 2:0
1900/1901 1. Round Chesterfield FC - Middlesbrough FC 2:3
1899/1900 7. Round Middlesbrough FC - Chesterfield FC 0:1
1899/1900 5. Round Chesterfield FC - Middlesbrough FC 7:1
FA Cup
1996/1997 Semi-finals Chesterfield FC - Middlesbrough FC 0:3 (0:1)
1996/1997 Semi-finals Middlesbrough FC - Chesterfield FC 3:3 (0:0, 2:2) aet
1949/1950 4. Round Chesterfield FC - Middlesbrough FC 3:2
1946/1947 4. Round Middlesbrough FC - Chesterfield FC 2:1
1929/1930 3. Round Middlesbrough FC - Chesterfield FC 4:3
1929/1930 3. Round Chesterfield FC - Middlesbrough FC 1:1
1894/1895 1. Round Middlesbrough FC - Chesterfield FC 4:0
League Cup
2010/2011 1. Round Chesterfield FC - Middlesbrough FC 1:2 (0:2)
1999/2000 2. Round Middlesbrough FC - Chesterfield FC 2:1 (1:0)
1999/2000 2. Round Chesterfield FC - Middlesbrough FC 0:0 (0:0)
1983/1984 1. Round Chesterfield FC - Middlesbrough FC 5:3 pso
1983/1984 1. Round Middlesbrough FC - Chesterfield FC 0:1

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