Head to Head
| 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 |
| England League 1 | 2015/10/20 18:45 | Chesterfield v Southend | W | 3-0 |
Home History
| England National League | 2022/09/03 14:00 | Oldham v Chesterfield | W | 0-2 |
| England National League | 2022/08/29 14:00 | Altrincham v Chesterfield | W | 1-2 |
| England National League | 2022/08/26 18:45 | Chesterfield v Barnet | W | 3-1 |
| England National League | 2022/08/20 16:20 | Notts County v Chesterfield | D | 2-2 |
| England National League | 2022/08/16 18:45 | Chesterfield v Wrexham | W | 2-0 |
| England National League | 2022/08/13 14:00 | Chesterfield v Aldershot | W | 1-0 |
| England National League | 2022/08/06 14:00 | Dorking Wanderers v Chesterfield | D | 2-2 |
| Club Friendly List | 2022/07/29 18:00 | Boston Utd v Chesterfield | W | 0-2 |
Away History
| England National League | 2022/09/03 14:00 | Southend v Torquay | L | 1-2 |
| England National League | 2022/08/29 14:00 | Southend v Maidenhead Utd | W | 2-0 |
| England National League | 2022/08/27 14:00 | Eastleigh v Southend | L | 2-1 |
| England National League | 2022/08/20 14:00 | Southend v Oldham | W | 1-0 |
| England National League | 2022/08/16 18:45 | Halifax v Southend | D | 0-0 |
| England National League | 2022/08/13 14:00 | Solihull Moors v Southend | D | 1-1 |
| England National League | 2022/08/06 14:00 | Southend v Boreham Wood | L | 0-1 |
| Club Friendly List | 2022/07/26 18:00 | Ipswich v Southend | L | 3-1 |