| August | ||||
|---|---|---|---|---|
| 9 Aug, 15:00 | Barnet 1 - 3 Chesterfield | League Two | ||
| 12 Aug, 19:45 | Preston North End 2 - 0 Chesterfield | Carling Cup | ||
| 16 Aug, 15:00 | Chesterfield 1 - 3 Bury | League Two | ||
| 23 Aug, 12:00 | Grimsby Town 0 - 1 Chesterfield | League Two | ||
| 30 Aug, 15:00 | Chesterfield 0 - 1 Wycombe Wanderers | League Two | ||
| September | ||||
|---|---|---|---|---|
| 6 Sep, 15:00 | Chesterfield 1 - 0 Rotherham United | League Two | ||
| 13 Sep, 15:00 | Dagenham and Redbridge 3 - 0 Chesterfield | League Two | ||
| 20 Sep, 15:00 | Rochdale 2 - 1 Chesterfield | League Two | ||
| 27 Sep, 15:00 | Chesterfield 0 - 1 Brentford | League Two | ||
| October | ||||
|---|---|---|---|---|
| 4 Oct, 15:00 | Morecambe 2 - 2 Chesterfield | League Two | ||
| 11 Oct, 15:00 | Chesterfield v Chester City | League Two | ||
| 18 Oct, 15:00 | Lincoln City v Chesterfield | League Two | ||
| 22 Oct, 19:45 | Chesterfield v Aldershot Town | League Two | ||
| 25 Oct, 15:00 | Chesterfield v Notts County | League Two | ||
| 28 Oct, 19:45 | Exeter City v Chesterfield | League Two | ||
| November | ||||
|---|---|---|---|---|
| 1 Nov, 15:00 | Bournemouth v Chesterfield | League Two | ||
| 15 Nov, 15:00 | Chesterfield v Shrewsbury Town | League Two | ||
| 22 Nov, 15:00 | Chesterfield v Accrington | League Two | ||
| 25 Nov, 19:45 | Bradford City v Chesterfield | League Two | ||
| December | ||||
|---|---|---|---|---|
| 6 Dec, 15:00 | Gillingham v Chesterfield | League Two | ||
| 13 Dec, 15:00 | Chesterfield v Macclesfield Town | League Two | ||
| 20 Dec, 15:00 | Port Vale v Chesterfield | League Two | ||
| 26 Dec, 15:00 | Chesterfield v Luton Town | League Two | ||
| January | ||||
|---|---|---|---|---|
| 3 Jan, 15:00 | Brentford v Chesterfield | League Two | ||
| 10 Jan, 15:00 | Chesterfield v Rochdale | League Two | ||
| 17 Jan, 15:00 | Chester City v Chesterfield | League Two | ||
| 24 Jan, 15:00 | Chesterfield v Morecambe | League Two | ||
| 28 Jan, 19:45 | Chesterfield v Exeter City | League Two | ||
| 31 Jan, 15:00 | Notts County v Chesterfield | League Two | ||
| February | ||||
|---|---|---|---|---|
| 3 Feb, 19:45 | Aldershot Town v Chesterfield | League Two | ||
| 7 Feb, 15:00 | Chesterfield v Lincoln City | League Two | ||
| 14 Feb, 15:00 | Shrewsbury Town v Chesterfield | League Two | ||
| 21 Feb, 15:00 | Chesterfield v Bournemouth | League Two | ||
| 28 Feb, 15:00 | Chesterfield v Barnet | League Two | ||
| March | ||||
|---|---|---|---|---|
| 3 Mar, 19:45 | Bury v Chesterfield | League Two | ||
| 7 Mar, 15:00 | Wycombe Wanderers v Chesterfield | League Two | ||
| 11 Mar, 19:45 | Chesterfield v Grimsby Town | League Two | ||
| 14 Mar, 15:00 | Chesterfield v Dagenham and Redbridge | League Two | ||
| 21 Mar, 15:00 | Rotherham United v Chesterfield | League Two | ||
| 28 Mar, 15:00 | Chesterfield v Port Vale | League Two | ||
| April | ||||
|---|---|---|---|---|
| 4 Apr, 15:00 | Macclesfield Town v Chesterfield | League Two | ||
| 11 Apr, 15:00 | Chesterfield v Darlington | League Two | ||
| 13 Apr, 19:45 | Luton Town v Chesterfield | League Two | ||
| 18 Apr, 15:00 | Chesterfield v Gillingham | League Two | ||
| 25 Apr, 15:00 | Accrington v Chesterfield | League Two | ||
| May | ||||
|---|---|---|---|---|
| 2 May, 15:00 | Chesterfield v Bradford City | League Two | ||