Key: Win : Draw : Loss
| Date | Home | Away | Ref | ||
|---|---|---|---|---|---|
| 06/08/2016 | Oxford | 1 | 1 | Chesterfield | G Ward |
| 13/08/2016 | Chesterfield | 3 | 1 | Swindon | C Boyeson |
| 16/08/2016 | Chesterfield | 2 | 0 | Walsall | G Salisbury |
| 20/08/2016 | Shrewsbury | 2 | 1 | Chesterfield | B Toner |
| 27/08/2016 | Chesterfield | 1 | 3 | Millwall | L Probert |
| 03/09/2016 | AFC Wimbledon | 2 | 1 | Chesterfield | K Johnson |
| 10/09/2016 | Oldham | 0 | 0 | Chesterfield | M Heywood |
| 17/09/2016 | Chesterfield | 3 | 1 | Northampton | R Jones |
| 24/09/2016 | Bury | 2 | 1 | Chesterfield | D Whitestone |
| 27/09/2016 | Chesterfield | 3 | 3 | Gillingham | T Kettle |
| 01/10/2016 | Chesterfield | 0 | 1 | Bradford | D Bond |
| 15/10/2016 | Southend | 1 | 0 | Chesterfield | K Johnson |
| 18/10/2016 | Chesterfield | 0 | 1 | Fleetwood Town | R Joyce |
| 22/10/2016 | Chesterfield | 0 | 3 | Scunthorpe | O Langford |
| 29/10/2016 | Charlton | 1 | 0 | Chesterfield | J Busby |
| 01/11/2016 | Coventry | 2 | 0 | Chesterfield | J Brooks |
| 13/11/2016 | Chesterfield | 1 | 4 | Sheffield United | C Sarginson |
| 19/11/2016 | Fleetwood Town | 2 | 1 | Chesterfield | S Stockbridge |
| 22/11/2016 | Milton Keynes Dons | 2 | 3 | Chesterfield | G Ward |
| 26/11/2016 | Chesterfield | 3 | 2 | Bristol Rvs | A Haines |
| 10/12/2016 | Peterboro | 5 | 2 | Chesterfield | N Miller |
| 17/12/2016 | Chesterfield | 1 | 0 | Bolton | M Haywood |
| 26/12/2016 | Rochdale | 3 | 0 | Chesterfield | C Boyeson |
| 30/12/2016 | Port Vale | 1 | 0 | Chesterfield | M Salisbury |
| 02/01/2017 | Chesterfield | 0 | 0 | Milton Keynes Dons | D England |
| 07/01/2017 | Bradford | 2 | 0 | Chesterfield | T Kettle |
| 14/01/2017 | Chesterfield | 1 | 0 | Coventry | N Kinseley |
| 21/01/2017 | Chesterfield | 0 | 0 | AFC Wimbledon | E Ilderton |
| 04/02/2017 | Chesterfield | 0 | 1 | Oldham | R Joyce |
| 11/02/2017 | Northampton | 3 | 1 | Chesterfield | R Clark |
| 14/02/2017 | Gillingham | 1 | 1 | Chesterfield | G Horwood |
| 18/02/2017 | Chesterfield | 1 | 2 | Bury | S Hooper |
| 21/02/2017 | Millwall | 0 | 0 | Chesterfield | L Collins |
| 25/02/2017 | Chesterfield | 0 | 4 | Oxford | D Webb |
| 04/03/2017 | Swindon | 0 | 1 | Chesterfield | C Sarginson |
| 07/03/2017 | Walsall | 1 | 0 | Chesterfield | R Lewis |
| 11/03/2017 | Chesterfield | 1 | 1 | Shrewsbury | A Haines |
| 14/03/2017 | Chesterfield | 3 | 3 | Peterboro | S Stockbridge |
| 18/03/2017 | Bristol Rvs | 2 | 1 | Chesterfield | D Handley |
| 25/03/2017 | Chesterfield | 1 | 3 | Rochdale | M Brown |
| 01/04/2017 | Bolton | 0 | 0 | Chesterfield | E Ilderton |
| 08/04/2017 | Chesterfield | 1 | 0 | Port Vale | R Clark |
| 14/04/2017 | Chesterfield | 0 | 4 | Southend | R Joyce |
| 17/04/2017 | Scunthorpe | 3 | 1 | Chesterfield | D Drysdale |
| 22/04/2017 | Chesterfield | 1 | 2 | Charlton | M Salisbury |
| 30/04/2017 | Sheffield United | 3 | 2 | Chesterfield | J Busby |