[14] Southend 3-3 Portsmouth [4] 2019-02-16 12:30
Weather: Good Stadium: Roots Hall Pitch: Good Round: 33
Referee: Dean Whitestone Home Manager: Chris Powell Away Manager: Kenneth Francis Jackett
Head to Head
| England EFL Trophy | 2019/01/08 19:45 | Southend v Portsmouth | L | 0-2 |
| England League 1 | 2018/12/08 15:00 | Portsmouth v Southend | L | 2-0 |
| England League 1 | 2018/02/17 15:00 | Southend v Portsmouth | W | 3-1 |
| England League 1 | 2017/11/18 15:00 | Portsmouth v Southend | L | 1-0 |
| England League 2 | 2015/01/24 15:00 | Portsmouth v Southend | W | 1-2 |
| England League 2 | 2014/09/13 14:00 | Southend v Portsmouth | W | 2-0 |
Home History
| England League 1 | 2019/02/12 19:45 | Doncaster v Southend | L | 3-0 |
| England League 1 | 2019/02/09 15:00 | Charlton v Southend | D | 1-1 |
| England League 1 | 2019/02/02 15:00 | Southend v Bristol Rovers | L | 1-2 |
| England League 1 | 2019/01/26 15:00 | Southend v Luton | L | 0-1 |
| England League 1 | 2019/01/19 15:00 | Bradford v Southend | W | 0-4 |
| England League 1 | 2019/01/12 15:00 | Southend v Plymouth | L | 2-3 |
| England EFL Trophy | 2019/01/08 19:45 | Southend v Portsmouth | L | 0-2 |
| England League 1 | 2019/01/01 15:00 | Southend v Gillingham | W | 2-0 |
Away History
| England League 1 | 2019/02/09 15:00 | Plymouth v Portsmouth | D | 1-1 |
| England FA Cup | 2019/02/05 19:45 | QPR v Portsmouth | L | 2-0 |
| England League 1 | 2019/02/02 15:00 | Portsmouth v Doncaster | D | 1-1 |
| England League 1 | 2019/01/29 19:45 | Luton v Portsmouth | L | 3-2 |
| England FA Cup | 2019/01/26 15:00 | Portsmouth v QPR | D | 1-1 |
| England EFL Trophy | 2019/01/22 19:00 | Portsmouth v Peterborough | W | 1-0 |
| England League 1 | 2019/01/19 15:00 | Oxford Utd v Portsmouth | L | 2-1 |
| England League 1 | 2019/01/12 15:00 | Portsmouth v Blackpool | L | 0-1 |