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 | Chesterfield |
| 27/04/19 16:00 | Maidenhead United - : - Chesterfield |
| 22/04/19 16:00 | Chesterfield - : - Boreham Wood |
| 19/04/19 16:00 | Gateshead - : - Chesterfield |
| 13/04/19 16:00 | Chesterfield - : - Maidstone United |
| 06/04/19 16:00 | Dover Athletic - : - Chesterfield |
| 30/03/19 16:00 | Chesterfield - : - Dagenham & Redbridge |
| 23/03/19 16:00 | Chesterfield - : - Sutton United |
| 16/03/19 16:00 | Havant & Waterlooville - : - Chesterfield |
| 12/03/19 20:45 | Bromley - : - Chesterfield |
| 09/03/19 16:00 | Chesterfield - : - Eastleigh |
| 02/03/19 16:00 | Wrexham - : - Chesterfield |
| 23/02/19 16:00 | Chesterfield - : - Harrogate Town |
| 16/02/19 16:00 | Fylde - : - Chesterfield |
| 09/02/19 16:00 | Chesterfield - : - Halifax Town |
| 02/02/19 16:00 | Braintree Town - : - Chesterfield |
| 26/01/19 16:00 | Chesterfield - : - Barrow |
| 19/01/19 16:00 | Aldershot Town - : - Chesterfield |
| 05/01/19 16:00 | Chesterfield - : - Ebbsfleet United |
| 01/01/19 16:00 | Solihull Moors - : - Chesterfield |
| 29/12/18 16:00 | Chesterfield - : - Hartlepool United |
| 26/12/18 16:00 | Chesterfield - : - Solihull Moors |
| 22/12/18 16:00 | Leyton Orient - : - Chesterfield |
| 08/12/18 16:00 | Chesterfield - : - Salford City |
| 01/12/18 16:00 | Barnet - : - Chesterfield |
| 27/11/18 20:45 | Chesterfield - : - Bromley |
| 24/11/18 16:00 | Eastleigh - : - Chesterfield |
| 17/11/18 16:00 | Chesterfield - : - Havant & Waterlooville |  |
| 10/11/18 16:00 | Chesterfield 1 : 1 Billericay Town |
| 03/11/18 16:00 | Harrogate Town 1 : 1 Chesterfield | |
| 30/10/18 20:45 | Sutton United 1 : 1 Chesterfield | |
| 27/10/18 16:00 | Chesterfield 1 : 1 Wrexham | |
| 20/10/18 16:00 | Fylde 1 : 3 Chesterfield |
| 13/10/18 18:15 | Halifax Town 1 : 1 Chesterfield | |
| 06/10/18 16:00 | Chesterfield 0 : 0 Fylde | |
| 29/09/18 16:00 | Maidstone United 1 : 1 Chesterfield | |
| 25/09/18 20:45 | Chesterfield 1 : 3 Maidenhead United | |
| 22/09/18 16:00 | Chesterfield 0 : 3 Gateshead | |
| 15/09/18 16:00 | Dagenham & Redbridge 1 : 1 Chesterfield | |
| 08/09/18 16:00 | Chesterfield 0 : 0 Dover Athletic | |
| 04/09/18 20:45 | Boreham Wood 1 : 0 Chesterfield | |
| 01/09/18 16:00 | Chesterfield 0 : 1 Leyton Orient | |
| 27/08/18 16:00 | Hartlepool United 1 : 0 Chesterfield | |
| 25/08/18 16:00 | Chesterfield 0 : 1 Barnet | |
| 18/08/18 16:00 | Salford City 3 : 2 Chesterfield | |
| 14/08/18 20:45 | Barrow 3 : 2 Chesterfield | |
| 11/08/18 16:00 | Chesterfield 1 : 0 Braintree Town | |
| 07/08/18 20:45 | Chesterfield 3 : 0 Aldershot Town | |
| 04/08/18 16:00 | Ebbsfleet United 0 : 1 Chesterfield | |
| 28/07/18 16:00 | Alfreton Town 2 : 0 Chesterfield |
| 25/07/18 20:00 | Chesterfield 1 : 1 Wigan Athletic |
| 14/07/18 16:00 | Boston United 1 : 1 Chesterfield |
| 05/05/18 16:00 | Barnet 3 : 0 Chesterfield | |
| 01/05/18 20:45 | Chesterfield 1 : 0 Newport County | |
| 28/04/18 16:00 | Chesterfield 1 : 2 Wycombe Wanderers | |
| 21/04/18 16:00 | Forest Green Rovers 4 : 1 Chesterfield | |
| 17/04/18 20:45 | Exeter City 2 : 1 Chesterfield | |
| 14/04/18 14:00 | Chesterfield 0 : 1 Mansfield Town | |
| 10/04/18 20:45 | Morecambe 2 : 2 Chesterfield | |
| 07/04/18 16:00 | Grimsby Town 1 : 0 Chesterfield | |
| 30/03/18 16:00 | Port Vale 2 : 1 Chesterfield | |
| 25/03/18 14:30 | Chesterfield 3 : 1 Nottingham County | |
| 17/03/18 16:00 | Cheltenham Town 1 : 1 Chesterfield | |
| 10/03/18 16:00 | Chesterfield 1 : 3 Lincoln City | |
| 24/02/18 16:00 | Chesterfield 2 : 1 Swindon Town | |
| 17/02/18 16:00 | Carlisle United 2 : 0 Chesterfield | |
| 13/02/18 20:45 | Chesterfield 2 : 3 Cambridge United | |
| 03/02/18 16:00 | Chesterfield 1 : 2 Crawley Town | |
| 27/01/18 16:00 | Chesterfield 0 : 1 Stevenage | |
| 20/01/18 16:00 | Yeovil Town 1 : 2 Chesterfield | |
| 13/01/18 16:00 | Chesterfield 2 : 0 Luton Town | |
| 06/01/18 16:00 | Accrington Stanley 4 : 0 Chesterfield | |
| 01/01/18 16:00 | Coventry City 1 : 0 Chesterfield | |
| 30/12/17 16:00 | Chesterfield 0 : 0 Colchester United | |
| 26/12/17 16:00 | Chesterfield 0 : 2 Crewe Alexandra | |
| 23/12/17 16:00 | Stevenage 5 : 1 Chesterfield | |
| 16/12/17 16:00 | Wycombe Wanderers 1 : 0 Chesterfield | |
| 09/12/17 16:00 | Chesterfield 2 : 1 Barnet | |
| 05/12/17 20:45 | Fleetwood Town 2 : 0 Chesterfield |
| 29/11/17 20:00 | Chesterfield 2 : 2 Manchester City U23 |
| 25/11/17 14:00 | Mansfield Town 2 : 2 Chesterfield | |
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