Head to Head
| England League 1 | 2017/04/14 14:00 | Chesterfield v Southend | W | 0-4 |
| England League 1 | 2016/10/15 14:00 | Southend v Chesterfield | W | 1-0 |
| England League 1 | 2016/03/05 15:00 | Southend v Chesterfield | L | 0-1 |
| England League 1 | 2015/10/20 18:45 | Chesterfield v Southend | L | 3-0 |
Home History
| England National League | 2021/10/05 18:45 | Southend v Eastleigh | W | 1-0 |
| England National League | 2021/10/02 14:00 | Solihull Moors v Southend | L | 2-0 |
| England National League | 2021/09/18 14:00 | Torquay v Southend | L | 1-0 |
| England National League | 2021/09/14 18:45 | Southend v Aldershot | L | 2-3 |
| England National League | 2021/09/11 14:00 | Halifax v Southend | L | 3-1 |
| England National League | 2021/09/04 14:00 | Southend v Wrexham | D | 2-2 |
| England National League | 2021/08/30 14:00 | Wealdstone v Southend | D | 0-0 |
| England National League | 2021/08/28 16:20 | Southend v Stockport | L | 0-1 |
Away History
| England National League | 2021/10/05 18:45 | Wrexham v Chesterfield | D | 1-1 |
| England National League | 2021/09/28 18:45 | Woking v Chesterfield | L | 3-1 |
| England National League | 2021/09/25 16:20 | Chesterfield v Torquay | D | 2-2 |
| England National League | 2021/09/18 14:00 | Yeovil v Chesterfield | W | 0-2 |
| England National League | 2021/09/14 18:45 | Chesterfield v Barnet | W | 4-2 |
| England National League | 2021/09/11 14:00 | Dover v Chesterfield | D | 0-0 |
| England National League | 2021/09/04 14:00 | Chesterfield v Bromley | D | 2-2 |
| England National League | 2021/08/30 14:00 | Kings Lynn Town v Chesterfield | W | 0-2 |