Key: Win : Draw : Loss
| Date | Home | Away | Ref | ||
|---|---|---|---|---|---|
| 03/08/2013 | Bury | 0 | 2 | Chesterfield | M Haywood |
| 10/08/2013 | Chesterfield | 2 | 0 | Cheltenham | M Bull |
| 17/08/2013 | Rochdale | 2 | 2 | Chesterfield | A Haines |
| 24/08/2013 | Chesterfield | 2 | 1 | Southend | S Stockbridge |
| 31/08/2013 | Portsmouth | 0 | 2 | Chesterfield | S Bratt |
| 07/09/2013 | Chesterfield | 1 | 0 | Accrington | D Deadman |
| 14/09/2013 | Chesterfield | 2 | 0 | AFC Wimbledon | E Ilderton |
| 21/09/2013 | Oxford | 0 | 1 | Chesterfield | T Kettle |
| 28/09/2013 | Chesterfield | 0 | 1 | Mansfield | R Madley |
| 05/10/2013 | Morecambe | 4 | 3 | Chesterfield | S Rushton |
| 12/10/2013 | Fleetwood Town | 1 | 1 | Chesterfield | R Lewis |
| 19/10/2013 | Chesterfield | 0 | 2 | Burton | D Webb |
| 22/10/2013 | Chesterfield | 2 | 2 | York | M Brown |
| 26/10/2013 | Bristol Rvs | 0 | 0 | Chesterfield | I Williamson |
| 02/11/2013 | Chesterfield | 1 | 1 | Scunthorpe | S Duncan |
| 16/11/2013 | Torquay | 0 | 2 | Chesterfield | D Sheldrake |
| 23/11/2013 | Chesterfield | 2 | 0 | Wycombe | A Woolmer |
| 26/11/2013 | Chesterfield | 0 | 0 | Northampton | D Drysdale |
| 01/12/2013 | Newport County | 3 | 2 | Chesterfield | M Haywood |
| 14/12/2013 | Chesterfield | 2 | 0 | Plymouth | A Haines |
| 20/12/2013 | Exeter | 0 | 2 | Chesterfield | C Berry |
| 26/12/2013 | Chesterfield | 1 | 1 | Hartlepool | G Sutton |
| 29/12/2013 | Chesterfield | 1 | 1 | Dag and Red | R Clark |
| 11/01/2014 | Chesterfield | 4 | 0 | Bury | T Harrington |
| 18/01/2014 | Southend | 3 | 0 | Chesterfield | R Madley |
| 21/01/2014 | Chesterfield | 2 | 2 | Rochdale | A D'Urso |
| 25/01/2014 | Northampton | 1 | 3 | Chesterfield | G Horwood |
| 28/01/2014 | York | 0 | 2 | Chesterfield | D Bond |
| 01/02/2014 | Chesterfield | 3 | 1 | Bristol Rvs | G Eltringham |
| 08/02/2014 | Scunthorpe | 1 | 1 | Chesterfield | L Mason |
| 15/02/2014 | Chesterfield | 3 | 1 | Torquay | C Boyeson |
| 22/02/2014 | Wycombe | 1 | 0 | Chesterfield | D Whitestone |
| 25/02/2014 | Cheltenham | 1 | 4 | Chesterfield | G Salisbury |
| 03/03/2014 | Chesterfield | 0 | 0 | Portsmouth | M Brown |
| 08/03/2014 | Accrington | 3 | 1 | Chesterfield | S Mathieson |
| 11/03/2014 | AFC Wimbledon | 1 | 1 | Chesterfield | D Deadman |
| 15/03/2014 | Chesterfield | 3 | 0 | Oxford | P Tierney |
| 18/03/2014 | Plymouth | 2 | 1 | Chesterfield | O Langford |
| 22/03/2014 | Mansfield | 0 | 0 | Chesterfield | D Bond |
| 25/03/2014 | Chesterfield | 1 | 0 | Morecambe | M Naylor |
| 05/04/2014 | Chesterfield | 1 | 1 | Newport County | S Hooper |
| 12/04/2014 | Hartlepool | 1 | 2 | Chesterfield | E Ilderton |
| 18/04/2014 | Chesterfield | 1 | 1 | Exeter | R Lewis |
| 21/04/2014 | Dag and Red | 0 | 1 | Chesterfield | S Bratt |
| 27/04/2014 | Burton | 0 | 2 | Chesterfield | R Madley |
| 03/05/2014 | Chesterfield | 2 | 1 | Fleetwood Town | A Madley |