Head to Head
| 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 | 2021/12/11 15:00 | Grimsby v Chesterfield | W | 0-1 |
| England FA Cup | 2021/12/05 17:15 | Salford City v Chesterfield | W | 0-2 |
| England National League | 2021/11/23 19:45 | Chesterfield v Altrincham | D | 2-2 |
| England National League | 2021/11/20 15:00 | Solihull Moors v Chesterfield | W | 0-2 |
| England National League | 2021/11/13 15:00 | Chesterfield v Weymouth | W | 4-0 |
| England FA Cup | 2021/11/06 15:00 | Chesterfield v Southend | W | 3-1 |
| England National League | 2021/10/30 14:00 | Dag & Red v Chesterfield | D | 2-2 |
| England National League | 2021/10/26 18:45 | Chesterfield v Eastleigh | W | 1-0 |
Away History
| England FA Trophy | 2021/12/18 15:00 | Southend v Dorking Wanderers | W | 2-1 |
| England National League | 2021/12/11 15:00 | Notts County v Southend | L | 4-1 |
| England National League | 2021/12/07 19:45 | Southend v Maidenhead Utd | D | 1-1 |
| England National League | 2021/11/27 15:00 | Altrincham v Southend | W | 1-2 |
| England National League | 2021/11/19 19:45 | Grimsby v Southend | L | 1-0 |
| England National League | 2021/11/13 15:00 | Southend v Woking | L | 0-2 |
| England FA Cup | 2021/11/06 15:00 | Chesterfield v Southend | L | 3-1 |
| England National League | 2021/11/02 19:45 | Southend v Dover | W | 4-1 |