Head to Head
| England National League | 2022/09/13 18:45 | Chesterfield v Southend | L | 3-2 |
| England National League | 2022/03/05 15:00 | Chesterfield v Southend | D | 2-2 |
| England FA Cup | 2021/11/06 15:00 | Chesterfield v Southend | L | 3-1 |
| England National League | 2021/10/09 14:00 | Southend v Chesterfield | L | 0-4 |
| 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 |