Key: Win : Draw : Loss
| Date | Home | Away | Ref | ||
|---|---|---|---|---|---|
| 07/08/2010 | Chesterfield | 2 | 1 | Barnet | G Eltringham |
| 14/08/2010 | Port Vale | 1 | 1 | Chesterfield | K Evans |
| 21/08/2010 | Chesterfield | 4 | 0 | Hereford | M Brown |
| 28/08/2010 | Macclesfield | 1 | 1 | Chesterfield | P Gibbs |
| 04/09/2010 | Chesterfield | 2 | 1 | Lincoln | M Russell |
| 11/09/2010 | Morecambe | 1 | 1 | Chesterfield | A Bates |
| 18/09/2010 | Chesterfield | 3 | 0 | Cheltenham | R Madley |
| 25/09/2010 | Rotherham | 1 | 0 | Chesterfield | A Haines |
| 28/09/2010 | Northampton | 1 | 2 | Chesterfield | A D'Urso |
| 02/10/2010 | Chesterfield | 5 | 5 | Crewe | J Moss |
| 09/10/2010 | Chesterfield | 2 | 1 | Southend | D Coote |
| 16/10/2010 | Wycombe | 1 | 2 | Chesterfield | P Tierney |
| 23/10/2010 | Chesterfield | 4 | 3 | Shrewsbury | N Swarbrick |
| 30/10/2010 | Stevenage | 0 | 0 | Chesterfield | D McDermid |
| 02/11/2010 | Chesterfield | 5 | 2 | Accrington | D Whitestone |
| 13/11/2010 | Chesterfield | 1 | 2 | Burton | L Mason |
| 20/11/2010 | Aldershot | 0 | 2 | Chesterfield | G Hegley |
| 23/11/2010 | Chesterfield | 1 | 2 | Oxford | G Horwood |
| 11/12/2010 | Chesterfield | 1 | 0 | Torquay | J Moss |
| 01/01/2011 | Chesterfield | 4 | 1 | Stockport | T Kettle |
| 03/01/2011 | Accrington | 2 | 2 | Chesterfield | M Haywood |
| 08/01/2011 | Southend | 2 | 3 | Chesterfield | R East |
| 15/01/2011 | Chesterfield | 1 | 0 | Stevenage | D Webb |
| 22/01/2011 | Shrewsbury | 0 | 0 | Chesterfield | S Mathieson |
| 25/01/2011 | Gillingham | 0 | 2 | Chesterfield | D Drysdale |
| 29/01/2011 | Chesterfield | 2 | 2 | Bradford | G Scott |
| 01/02/2011 | Stockport | 1 | 1 | Chesterfield | M Naylor |
| 05/02/2011 | Chesterfield | 2 | 2 | Aldershot | A Taylor |
| 11/02/2011 | Burton | 1 | 0 | Chesterfield | D Sheldrake |
| 15/02/2011 | Bury | 1 | 1 | Chesterfield | D Foster |
| 19/02/2011 | Lincoln | 0 | 2 | Chesterfield | R Lewis |
| 22/02/2011 | Bradford | 0 | 1 | Chesterfield | K Evans |
| 26/02/2011 | Chesterfield | 0 | 2 | Morecambe | B Malone |
| 01/03/2011 | Chesterfield | 4 | 1 | Wycombe | S Rushton |
| 05/03/2011 | Cheltenham | 0 | 3 | Chesterfield | P Tierney |
| 08/03/2011 | Chesterfield | 2 | 1 | Northampton | P Quinn |
| 12/03/2011 | Crewe | 2 | 0 | Chesterfield | G Ward |
| 18/03/2011 | Chesterfield | 5 | 0 | Rotherham | A D'Urso |
| 26/03/2011 | Barnet | 2 | 2 | Chesterfield | P Miller |
| 02/04/2011 | Chesterfield | 2 | 0 | Port Vale | S Tanner |
| 09/04/2011 | Hereford | 3 | 0 | Chesterfield | C Sarginson |
| 16/04/2011 | Chesterfield | 2 | 1 | Macclesfield | G Horwood |
| 23/04/2011 | Oxford | 0 | 0 | Chesterfield | G Salisbury |
| 25/04/2011 | Chesterfield | 2 | 3 | Bury | K Friend |
| 29/04/2011 | Torquay | 0 | 0 | Chesterfield | D Coote |
| 07/05/2011 | Chesterfield | 3 | 1 | Gillingham | T Kettle |