- Chesterfield 0-3 Scunthorpe United – League 1 (22/10/16)
- Chesterfield 0-1 Fleetwood Town – League 1 (18/10/16)
- Chesterfield 3-0 Rotherham United – Central League North East Division (11/10/16)
- Chesterfield 0-1 Bradford City – League 1 (01/10/16)
- Chesterfield 3-3 Gillingham- League 1 (27/09/16)
- Chesterfield 3-1 Northampton Town – League 1 (17/09/16)
- Chesterfield 1-3 Millwall – League 1 (27/08/16)
- Chesterfield 2-0 Walsall – League 1 (16/08/16)
- Chesterfield 3-1 Swindon Town – League 1 (13/08/16)
- Chesterfield 0-2 Sheffield Wednesday – Friendly (16/07/16)
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