- Chesterfield 1-1 Sheffield Wednesday – Friendly (27/07/13)
- Chesterfield 2-0 Cheltenham Town – League 2 (10/08/13)
- Chesterfield 2-1 Southend United – League 2 (24/08/13)
- Chesterfield 1-0 Accrington Stanley – League 2 (07/09/13)
- Chesterfield 2-0 AFC Wimbledon – League 2 (14/09/13)
- Chesterfield 0-1 Mansfield Town – League 2 (28/09/13)
- Chesterfield 0-2 Burton Albion – League 2 (19/10/13)
- Chesterfield 2-2 York City – League 2 (22/10/13)
- Chesterfield 1-1 Scunthorpe United – League 2 (02/11/13)
- Chesterfield 2-0 Daventry Town – FA Cup 1st Round (09/11/13)
- Chesterfield 3-0 Rochdale – JPT Area Quarter Final (12/11/13)
- Chesterfield 2-0 Wycombe Wanderers – League 2 (23/11/13)
- Chesterfield 0-0 Northampton Town – League 2 (26/11/13)
- Chesterfield 1-3 Southend United – FA Cup 2nd Round (07/12/13)
- Chesterfield 2-0 Plymouth Argyle – League 2 (14/12/13)
- Chesterfield 1-1 Hartlepool United – League 2 (26/12/13)
- Chesterfield 1-1 Dag & Red – League 2 (29/12/13)
- Chesterfield 4-0 Bury – League 2 (11/01/14)
- Chesterfield 2-2 Rochdale – League 2 (21/01/14)
- Chesterfield 3-1 Bristol Rovers – League 2 (01/02/14)
- Chesterfield 3-1 Torquay United – League 2 (15/02/14)
- Chesterfield 0-1 Fleetwood Town (3-2 agg) – JPT Area Final 2nd Leg (18/02/14)
- Chesterfield 0-0 Portsmouth – League 2 (03/03/14)
- Chesterfield 3-0 Oxford United – League 2 (15/03/14)
- Chesterfield 1-0 Morecambe – League 2 (25/03/14)
- Chesterfield 1-1 Newport County – League 2 (05/04/14)
- Chesterfield 1-1 Exeter City – League 2 (18/04/14)
- Chesterfield 2-1 Fleetwood Town – League 2 (03/05/14)
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