Head to Head
| 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 |
| England League 1 | 2016/03/05 15:00 | Southend v Chesterfield | W | 0-1 |
Home History
| England National League | 2023/08/28 14:00 | Chesterfield v Hartlepool | W | 3-2 |
| England National League | 2023/08/26 14:00 | Altrincham v Chesterfield | L | 2-1 |
| England National League | 2023/08/19 11:30 | Chesterfield v Oldham | D | 1-1 |
| England National League | 2023/08/15 18:45 | Oxford City v Chesterfield | W | 1-2 |
| England National League | 2023/08/12 14:00 | AFC Fylde v Chesterfield | W | 2-4 |
| England National League | 2023/08/05 14:00 | Chesterfield v Dorking Wanderers | W | 4-3 |
| Club Friendly List | 2023/07/29 12:00 | Bristol Rovers v Chesterfield | L | 2-0 |
| Club Friendly List | 2023/07/22 14:00 | Accrington Stanley v Chesterfield | W | 2-3 |
Away History
| England National League | 2023/08/28 14:00 | Bromley v Southend | L | 2-1 |
| England National League | 2023/08/25 18:45 | Southend v Eastleigh | W | 2-0 |
| England National League | 2023/08/19 14:00 | Southend v Hartlepool | L | 2-3 |
| England National League | 2023/08/15 18:45 | Dorking Wanderers v Southend | L | 2-1 |
| England National League | 2023/08/12 14:00 | Dag & Red v Southend | W | 0-2 |
| England National League | 2023/08/05 14:00 | Southend v Oldham | W | 4-0 |
| Club Friendly List | 2023/07/25 18:30 | Canvey Island v Southend | W | 0-1 |
| England National League | 2023/04/29 16:30 | Southend v Wealdstone | W | 2-1 |
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