Head to Head
| England National League | 2023/11/18 15:00 | Southend v Chesterfield | L | 2-1 |
| England National League | 2023/03/07 19:45 | Southend v Chesterfield | W | 1-2 |
| England National League | 2022/09/13 18:45 | Chesterfield v Southend | W | 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 | W | 3-1 |
| England National League | 2021/10/09 14:00 | Southend v Chesterfield | W | 0-4 |
| England League 1 | 2017/04/14 14:00 | Chesterfield v Southend | L | 0-4 |
| England League 1 | 2016/10/15 14:00 | Southend v Chesterfield | L | 1-0 |
Home History
| England National League | 2024/01/23 19:45 | Chesterfield v Woking | W | 1-0 |
| England National League | 2024/01/16 19:45 | Chesterfield v Altrincham | W | 2-1 |
| England FA Trophy | 2024/01/13 15:00 | Welling v Chesterfield | L | 2-0 |
| England National League | 2024/01/10 19:45 | Chesterfield v Gateshead | W | 5-0 |
| England FA Cup | 2024/01/06 15:00 | Watford v Chesterfield | L | 2-1 |
| England National League | 2024/01/01 15:00 | Chesterfield v Solihull Moors | W | 3-2 |
| England National League | 2023/12/26 15:00 | Solihull Moors v Chesterfield | L | 2-0 |
| England National League | 2023/12/23 15:00 | Chesterfield v Aldershot | W | 4-1 |
Away History
| England National League | 2024/01/13 15:00 | Eastleigh v Southend | W | 0-1 |
| England National League | 2024/01/06 15:00 | Southend v Halifax | W | 3-0 |
| England National League | 2023/12/30 15:00 | Barnet v Southend | L | 1-0 |
| England National League | 2023/12/26 15:00 | Southend v Barnet | L | 0-2 |
| England National League | 2023/12/23 15:00 | Kidderminster v Southend | W | 1-2 |
| England National League | 2023/12/16 15:00 | Southend v Bromley | L | 1-2 |
| England FA Trophy | 2023/12/09 15:00 | Southend v Hampton & Richmond | D | 2-2 |
| England National League | 2023/11/25 15:00 | Gateshead v Southend | D | 1-1 |