Key: Win : Draw : Loss
| Date | Home | Away | Ref | ||
|---|---|---|---|---|---|
| 05/08/2017 | Chesterfield | 1 | 3 | Grimsby | E Ilderton |
| 12/08/2017 | Notts County | 2 | 0 | Chesterfield | A Haines |
| 19/08/2017 | Chesterfield | 2 | 0 | Port Vale | T Nield |
| 26/08/2017 | Newport County | 4 | 1 | Chesterfield | D Webb |
| 02/09/2017 | Chesterfield | 0 | 0 | Coventry | D Drysdale |
| 09/09/2017 | Crewe | 5 | 1 | Chesterfield | M Coy |
| 12/09/2017 | Colchester | 1 | 1 | Chesterfield | D Handley |
| 16/09/2017 | Chesterfield | 1 | 2 | Accrington | C Hicks |
| 23/09/2017 | Luton | 1 | 0 | Chesterfield | C Breakspear |
| 26/09/2017 | Chesterfield | 2 | 3 | Yeovil | D Coote |
| 30/09/2017 | Chesterfield | 0 | 2 | Cheltenham | B Toner |
| 07/10/2017 | Lincoln | 2 | 1 | Chesterfield | J Brooks |
| 14/10/2017 | Chesterfield | 0 | 2 | Morecambe | D Drysdale |
| 17/10/2017 | Crawley Town | 0 | 2 | Chesterfield | N Kinseley |
| 21/10/2017 | Cambridge | 2 | 1 | Chesterfield | J Busby |
| 28/10/2017 | Chesterfield | 2 | 2 | Carlisle | B Huxtable |
| 11/11/2017 | Swindon | 2 | 2 | Chesterfield | L Collins |
| 18/11/2017 | Chesterfield | 1 | 0 | Exeter | M Coy |
| 21/11/2017 | Chesterfield | 3 | 2 | Forest Green | R Jones |
| 25/11/2017 | Mansfield | 2 | 2 | Chesterfield | A Woolmer |
| 09/12/2017 | Chesterfield | 2 | 1 | Barnet | J Busby |
| 16/12/2017 | Wycombe | 1 | 0 | Chesterfield | N Kinseley |
| 23/12/2017 | Stevenage | 5 | 1 | Chesterfield | C Hicks |
| 26/12/2017 | Chesterfield | 0 | 2 | Crewe | T Nield |
| 30/12/2017 | Chesterfield | 0 | 0 | Colchester | S Stockbridge |
| 01/01/2018 | Coventry | 1 | 0 | Chesterfield | T Kettle |
| 06/01/2018 | Accrington | 4 | 0 | Chesterfield | C Sarginson |
| 13/01/2018 | Chesterfield | 2 | 0 | Luton | C Boyeson |
| 20/01/2018 | Yeovil | 1 | 2 | Chesterfield | K Johnson |
| 27/01/2018 | Chesterfield | 0 | 1 | Stevenage | M Heywood |
| 03/02/2018 | Chesterfield | 1 | 2 | Crawley Town | R Joyce |
| 13/02/2018 | Chesterfield | 2 | 3 | Cambridge | D Handley |
| 17/02/2018 | Carlisle | 2 | 0 | Chesterfield | S Stockbridge |
| 24/02/2018 | Chesterfield | 2 | 1 | Swindon | J Brooks |
| 10/03/2018 | Chesterfield | 1 | 3 | Lincoln | D Webb |
| 17/03/2018 | Cheltenham | 1 | 1 | Chesterfield | O Yates |
| 25/03/2018 | Chesterfield | 3 | 1 | Notts County | S Stockbridge |
| 30/03/2018 | Port Vale | 2 | 1 | Chesterfield | T Harrington |
| 07/04/2018 | Grimsby | 1 | 0 | Chesterfield | R Madley |
| 10/04/2018 | Morecambe | 2 | 2 | Chesterfield | M Coy |
| 14/04/2018 | Chesterfield | 0 | 1 | Mansfield | D Drysdale |
| 17/04/2018 | Exeter | 2 | 1 | Chesterfield | B Malone |
| 21/04/2018 | Forest Green | 4 | 1 | Chesterfield | S Duncan |
| 28/04/2018 | Chesterfield | 1 | 2 | Wycombe | A Backhouse |
| 01/05/2018 | Chesterfield | 1 | 0 | Newport County | G Ward |
| 05/05/2018 | Barnet | 3 | 0 | Chesterfield | D Whitestone |