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 |
Home History
| England National League | 2023/03/03 19:45 | Southend v Barnet | L | 0-1 |
| England National League | 2023/02/25 15:00 | Torquay v Southend | W | 1-2 |
| England National League | 2023/02/21 19:45 | Notts County v Southend | L | 4-0 |
| England National League | 2023/02/18 15:00 | Southend v Gateshead | W | 1-0 |
| England National League | 2023/02/14 19:45 | Southend v Halifax | W | 2-1 |
| England FA Trophy | 2023/02/11 15:00 | Southend v York | L | 0-2 |
| England National League | 2023/02/07 19:45 | Maidenhead Utd v Southend | W | 1-2 |
| England National League | 2023/02/04 15:00 | Southend v York | W | 2-0 |
Away History
| England National League | 2023/03/04 15:00 | Gateshead v Chesterfield | W | 1-2 |
| England National League | 2023/02/28 19:45 | Wrexham v Chesterfield | L | 2-1 |
| England National League | 2023/02/25 15:00 | Chesterfield v Oldham | L | 0-1 |
| England National League | 2023/02/21 19:45 | Chesterfield v Wealdstone | D | 1-1 |
| England National League | 2023/02/18 15:00 | Solihull Moors v Chesterfield | D | 0-0 |
| England National League | 2023/02/14 19:45 | Aldershot v Chesterfield | D | 1-1 |
| England National League | 2023/02/11 17:20 | Chesterfield v Notts County | L | 1-2 |
| England National League | 2023/02/07 19:45 | Chesterfield v Woking | L | 1-3 |