Key: Win : Draw : Loss
| Date | Home | Away | Ref | ||
|---|---|---|---|---|---|
| 08/08/2015 | Chesterfield | 3 | 1 | Barnsley | A Woolmer |
| 15/08/2015 | Sheffield United | 2 | 0 | Chesterfield | K Wright |
| 18/08/2015 | Shrewsbury | 1 | 2 | Chesterfield | M Heywood |
| 22/08/2015 | Chesterfield | 0 | 0 | Rochdale | K Hill |
| 29/08/2015 | Millwall | 0 | 2 | Chesterfield | D Deadman |
| 05/09/2015 | Chesterfield | 2 | 3 | Wigan | M Brown |
| 12/09/2015 | Chesterfield | 3 | 3 | Colchester | I Williamson |
| 19/09/2015 | Coventry | 1 | 0 | Chesterfield | D Bond |
| 26/09/2015 | Chesterfield | 1 | 2 | Burton | D Webb |
| 29/09/2015 | Blackpool | 2 | 0 | Chesterfield | S Duncan |
| 03/10/2015 | Crewe | 1 | 2 | Chesterfield | R Joyce |
| 10/10/2015 | Chesterfield | 1 | 3 | Gillingham | N Kinseley |
| 17/10/2015 | Walsall | 1 | 2 | Chesterfield | C Kavanagh |
| 20/10/2015 | Chesterfield | 3 | 0 | Southend | G Salisbury |
| 24/10/2015 | Chesterfield | 0 | 3 | Scunthorpe | D England |
| 31/10/2015 | Fleetwood Town | 0 | 1 | Chesterfield | T Kettle |
| 14/11/2015 | Chesterfield | 1 | 2 | Oldham | T Robinson |
| 21/11/2015 | Port Vale | 3 | 2 | Chesterfield | M Bull |
| 24/11/2015 | Doncaster | 3 | 0 | Chesterfield | K Friend |
| 28/11/2015 | Chesterfield | 0 | 4 | Swindon | D Bond |
| 12/12/2015 | Bury | 1 | 0 | Chesterfield | P Bankes |
| 19/12/2015 | Chesterfield | 0 | 1 | Bradford | J Adcock |
| 26/12/2015 | Peterboro | 2 | 0 | Chesterfield | A Woolmer |
| 28/12/2015 | Chesterfield | 1 | 1 | Coventry | P Tierney |
| 02/01/2016 | Chesterfield | 7 | 1 | Shrewsbury | G Eltringham |
| 09/01/2016 | Rochdale | 2 | 3 | Chesterfield | C Boyeson |
| 16/01/2016 | Wigan | 3 | 1 | Chesterfield | R Joyce |
| 23/01/2016 | Chesterfield | 1 | 2 | Millwall | C Sarginson |
| 06/02/2016 | Chesterfield | 0 | 1 | Peterboro | D Coote |
| 12/02/2016 | Burton | 1 | 0 | Chesterfield | S Hooper |
| 16/02/2016 | Colchester | 1 | 1 | Chesterfield | L Swabey |
| 20/02/2016 | Chesterfield | 3 | 1 | Crewe | G Ward |
| 27/02/2016 | Gillingham | 1 | 2 | Chesterfield | K Johnson |
| 01/03/2016 | Chesterfield | 1 | 1 | Blackpool | E Ilderton |
| 05/03/2016 | Southend | 0 | 1 | Chesterfield | D Drysdale |
| 12/03/2016 | Chesterfield | 1 | 4 | Walsall | R Joyce |
| 19/03/2016 | Scunthorpe | 1 | 1 | Chesterfield | K Hill |
| 26/03/2016 | Chesterfield | 0 | 0 | Fleetwood Town | N Miller |
| 28/03/2016 | Oldham | 1 | 0 | Chesterfield | T Harrington |
| 02/04/2016 | Chesterfield | 4 | 2 | Port Vale | K Wright |
| 09/04/2016 | Barnsley | 1 | 2 | Chesterfield | N Swarbrick |
| 16/04/2016 | Chesterfield | 0 | 3 | Sheffield United | G Salisbury |
| 19/04/2016 | Chesterfield | 1 | 1 | Doncaster | J Simpson |
| 23/04/2016 | Swindon | 1 | 0 | Chesterfield | T Kettle |
| 30/04/2016 | Chesterfield | 3 | 0 | Bury | C Sarginson |
| 08/05/2016 | Bradford | 2 | 0 | Chesterfield | D Webb |