Head to Head
| Inglismaa National League | 2023/03/07 19:45 | Southend v Chesterfield | L | 1-2 |
| Inglismaa National League | 2022/09/13 18:45 | Chesterfield v Southend | L | 3-2 |
| Inglismaa National League | 2022/03/05 15:00 | Chesterfield v Southend | D | 2-2 |
| Inglismaa FA Cup | 2021/11/06 15:00 | Chesterfield v Southend | L | 3-1 |
| Inglismaa National League | 2021/10/09 14:00 | Southend v Chesterfield | L | 0-4 |
| Inglismaa League 1 | 2017/04/14 14:00 | Chesterfield v Southend | W | 0-4 |
| Inglismaa League 1 | 2016/10/15 14:00 | Southend v Chesterfield | W | 1-0 |
| Inglismaa League 1 | 2016/03/05 15:00 | Southend v Chesterfield | L | 0-1 |
Home History
| Inglismaa National League | 2023/11/11 15:00 | Altrincham v Southend | L | 2-0 |
| Inglismaa National League | 2023/10/28 14:00 | Boreham Wood v Southend | D | 1-1 |
| Inglismaa National League | 2023/10/24 18:45 | Southend v Ebbsfleet United | W | 3-0 |
| Inglismaa National League | 2023/10/21 14:00 | Southend v Solihull Moors | W | 5-0 |
| Inglismaa FA Cupi kvalifikatsioon | 2023/10/14 14:00 | Yeovil v Southend | L | 2-0 |
| Inglismaa National League | 2023/10/07 14:00 | Woking v Southend | W | 0-2 |
| Inglismaa National League | 2023/10/03 18:45 | Southend v Oxford City | W | 2-0 |
| Inglismaa National League | 2023/09/30 14:00 | Rochdale v Southend | D | 2-2 |
Away History
| Inglismaa National League | 2023/11/11 15:00 | Chesterfield v Barnet | W | 4-2 |
| Inglismaa FA Cup | 2023/11/05 12:15 | Chesterfield v Portsmouth | W | 1-0 |
| Inglismaa National League | 2023/10/28 14:00 | Kidderminster v Chesterfield | W | 1-3 |
| Inglismaa National League | 2023/10/24 18:45 | Chesterfield v York | W | 4-0 |
| Inglismaa FA Cupi kvalifikatsioon | 2023/10/14 14:00 | Chesterfield v Kettering | W | 5-0 |
| Inglismaa National League | 2023/10/07 14:00 | Boreham Wood v Chesterfield | W | 0-2 |
| Inglismaa National League | 2023/10/03 18:45 | Chesterfield v Bromley | W | 2-0 |
| Inglismaa National League | 2023/09/30 14:00 | Maidenhead Utd v Chesterfield | D | 1-1 |