Portsmouth Postponed Southend 2019-09-07 14:00
Stadium: Fratton Park Round: 7
Home Manager: Kenneth Francis Jackett Away Manager: Kevin Bond
Head to Head
| England - League 1 | 2019/02/16 12:30 | Southend v Portsmouth | D | 3-3 |
| England - EFL Trophy | 2019/01/08 19:45 | Southend v Portsmouth | W | 0-2 |
| England - League 1 | 2018/12/08 15:00 | Portsmouth v Southend | W | 2-0 |
| England - League 1 | 2018/02/17 15:00 | Southend v Portsmouth | L | 3-1 |
| England - League 1 | 2017/11/18 15:00 | Portsmouth v Southend | W | 1-0 |
| England - League 2 | 2015/01/24 15:00 | Portsmouth v Southend | L | 1-2 |
| England - League 2 | 2014/09/13 14:00 | Southend v Portsmouth | L | 2-0 |
Home History
| England - EFL Trophy | 2019/09/03 18:45 | Portsmouth v Crawley Town | W | 1-0 |
| England - League 1 | 2019/08/31 14:00 | Blackpool v Portsmouth | D | 1-1 |
| England - Ligacupen | 2019/08/28 18:45 | QPR v Portsmouth | W | 0-2 |
| England - League 1 | 2019/08/20 18:45 | Portsmouth v Coventry | D | 3-3 |
| England - League 1 | 2019/08/17 11:30 | Sunderland v Portsmouth | L | 2-1 |
| England - League 1 | 2019/08/10 14:00 | Portsmouth v Tranmere | W | 2-0 |
| England - Ligacupen | 2019/08/06 18:45 | Portsmouth v Birmingham | W | 3-0 |
| England - League 1 | 2019/08/03 14:00 | Shrewsbury v Portsmouth | L | 1-0 |
Away History
| England - EFL Trophy | 2019/09/03 18:45 | Leyton Orient v Southend | L | 2-0 |
| England - League 1 | 2019/08/31 14:00 | Southend v Rochdale | L | 0-3 |
| England - Ligacupen | 2019/08/27 18:45 | Southend v Milton Keynes Dons | L | 1-4 |
| England - League 1 | 2019/08/24 14:00 | Wycombe v Southend | L | 4-3 |
| England - League 1 | 2019/08/20 18:45 | Southend v Peterborough | L | 0-2 |
| England - League 1 | 2019/08/17 14:00 | Lincoln City v Southend | L | 4-0 |
| England - Ligacupen | 2019/08/13 18:45 | Stevenage v Southend | W | 1-2 |
| England - League 1 | 2019/08/10 14:00 | Southend v Blackpool | L | 1-3 |