Chesterfield 3-1 Southend 2021-08-17 09:00
Stadium: Proact Stadium Round: 7
Home Manager: James Colvin Rowe Away Manager: Kevin Andrew Maher
Head to Head
| 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
| UK Friendlies | 2021/08/14 13:00 | Chesterfield v Grimsby | W | 2-1 |
| Club Friendly List | 2021/07/31 14:00 | Chesterfield v Port Vale | L | 0-1 |
| Club Friendly List | 2021/07/27 18:30 | Chesterfield v Bradford | W | 2-1 |
| Club Friendly List | 2021/07/21 18:30 | Matlock Town v Chesterfield | W | 1-3 |
| UK Friendlies | 2021/07/17 14:00 | Alfreton Town v Chesterfield | L | 3-2 |
| England National League | 2021/06/05 15:00 | Notts County v Chesterfield | L | 3-2 |
| England National League | 2021/05/29 11:30 | Halifax v Chesterfield | W | 1-2 |
| England National League | 2021/05/22 14:00 | Chesterfield v Dag & Red | W | 2-1 |
Away History
| Club Friendly List | 2021/08/07 14:00 | Ebbsfleet United v Southend | D | 1-1 |
| Club Friendly List | 2021/08/04 18:00 | Southend v Brentford XI | L | 2-3 |
| UK Friendlies | 2021/07/31 14:00 | Dartford v Southend | D | 2-2 |
| England League 2 | 2021/05/08 14:00 | Southend v Newport County | D | 1-1 |
| England League 2 | 2021/05/01 14:00 | Barrow v Southend | W | 1-2 |
| England League 2 | 2021/04/24 14:00 | Southend v Leyton Orient | W | 2-1 |
| England League 2 | 2021/04/20 18:00 | Colchester v Southend | L | 2-0 |
| England League 2 | 2021/04/17 11:30 | Exeter v Southend | D | 0-0 |