| Date | Ground | Comp. | Match | Score | Attendance |
| 22/07/13 | Sandygate | Fr | Hallam v Chesterfield | 2-6 | 180 |
| 27/07/13 | Proact Stadium | Fr | Chesterfield v Sheffield Wednesday | 1-1 | 5,491 |
| 03/08/13 | Gigg Lane | L2 | Bury v Chesterfield | 0-2 | 4,337 |
| 07/08/13 | Elland Road | LC1 | Leeds United v Chesterfield | 2-1 | 17,466 |
| 10/08/13 | Proact Stadium | L2 | Chesterfield v Cheltenham Town | 2-0 | 5,367 |
| 13/08/13 | Bramall Lane | U21IFr | England U21 v Scotland U1 | 6-0 | 26,942 |
| 17/08/13 | Bramall Lane | L1 | Sheffield United v Colchester | 1-1 | 17,167 |
| 24/08/13 | Proact Stadium | L2 | Chesterfield v Southend U | 2-1 | 5,579 |
| 07/09/13 | Proact Stadium | L2 | Chesterfield v Accrington Stanley | 1-0 | 6,588 |
| 14/09/13 | Proact Stadium | L2 | Chesterfield v AFC Wimbledon | 2-0 | 6,353 |
| 28/09/13 | Proact Stadium | L2 | Chesterfield v Mansfield Town | 0-1 | 10,015 |
| 12/10/13 | Highbury Stadium | L2 | Fleetwood Town v Chesterfield | 1-1 | 4,521 |
| 19/10/13 | Proact Stadium | L2 | Chesterfield v Burton Albion | 0-2 | 6,901 |
| 22/10/13 | Proact Stadium | L2 | Chesterfield v York City | 2-2 | 5,907 |
| 02/11/13 | Proact Stadium | L2 | Chesterfield v Scunthorpe United | 1-1 | 6,346 |
| 09/11/13 | Proact Stadium | FAC1 | Chesterfield v Daventry Town | 2-0 | 5,269 |
| 12/11/13 | Proact Stadium | JPTAQF | Chesterfield v Rochdale | 3-0 | 2,897 |
| 23/11/13 | Proact Stadium | L2 | Chesterfield v Wycombe W | 2-0 | 5,798 |
| 26/11/13 | Proact Stadium | L2 | Chesterfield v Northampton | 0-0 | 5,321 |
| 07/12/13 | Proact Stadium | FAC2 | Chesterfield v Southend | 1-3 | 4,067 |
| 14/12/13 | Proact Stadium | L2 | Chesterfield v Plymouth | 2-0 | 5,486 |
| 26/12/13 | Proact Stadium | L2 | Chesterfield v Hartlepool | 1-1 | 7,680 |
| 29/12/13 | Proact Stadium | L2 | Chesterfield v Dag & Red | 1-1 | 5,906 |
| 11/01/14 | Proact Stadium | L2 | Chesterfield v Bury | 4-0 | 6,053 |
| 21/01/14 | Proact Stadium | L2 | Chesterfield v Rochdale | 2-2 | 5,078 |
| 25/01/14 | Etihad Stadium | FAC4 | Manchester City v Watford | 4-2 | 46,514 |
| 26/01/14 | Bramall Lane | FAC4 | Sheffield United v Fulham | 1-1 | 16,324 |
| 01/02/14 | Proact Stadium | L2 | Chesterfield v Bristol Rovers | 3-1 | 6,048 |
| 15/02/14 | Proact Stadium | L2 | Chesterfield v Torquay United | 3-1 | 5,012 |
| 18/02/14 | Proact Stadium | JPTAF2 | Chesterfield v Fleetwood Town | 0-1 (3-2agg) | 6,358 |
| 03/03/14 | Proact Stadium | L2 | Chesterfield v Portsmouth | 0-0 | 5,807 |
| 15/03/14 | Proact Stadium | L2 | Chesterfield v Oxford United | 3-0 | 6,246 |
| 25/03/14 | Proact Stadium | L2 | Chesterfield v Morecambe | 1-0 | 4,891 |
| 30/03/14 | Wembley Stadium | JPTF | Chesterfield v Peterborough | 1-3 | 35,663 |
| 05/04/14 | Proact Stadium | L2 | Chesterfield v Newport C | 1-1 | 5,659 |
| 18/04/14 | Proact Stadium | L2 | Chesterfield v Exeter City | 1-1 | 7,331 |
| 03/05/14 | Proact Stadium | L2 | Chesterfield v Fleetwood Town | 2-1 | 9,037 |
| 11/05/14 | Stadium of Light | Pr | Sunderland v Swansea City | 1-3 | 45,580 |
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