[2] Southend 0-2 Portsmouth [1] 2019-01-08 19:45
Weather: Good Stadium: Roots Hall Pitch: Good Round: 4
Head to Head
| 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 | 2019/01/01 15:00 | Southend v Gillingham | W | 2-0 |
| England League 1 | 2018/12/29 15:00 | Coventry v Southend | L | 1-0 |
| England League 1 | 2018/12/26 15:00 | Oxford Utd v Southend | W | 0-1 |
| England League 1 | 2018/12/22 15:00 | Southend v Rochdale | L | 1-2 |
| England League 1 | 2018/12/15 15:00 | Southend v Accrington Stanley | W | 3-0 |
| England League 1 | 2018/12/08 15:00 | Portsmouth v Southend | L | 2-0 |
| England EFL Trophy | 2018/12/05 19:45 | Luton v Southend | W | 3-5 |
| England FA Cup | 2018/12/01 15:00 | Southend v Barnsley | L | 2-4 |
Away History
| England FA Cup | 2019/01/05 17:30 | Norwich v Portsmouth | W | 0-1 |
| England League 1 | 2019/01/01 15:00 | Portsmouth v AFC Wimbledon | W | 2-1 |
| England League 1 | 2018/12/29 15:00 | Fleetwood Town v Portsmouth | W | 2-5 |
| England League 1 | 2018/12/26 13:00 | Gillingham v Portsmouth | L | 2-0 |
| England League 1 | 2018/12/22 15:00 | Portsmouth v Sunderland | W | 3-1 |
| England League 1 | 2018/12/15 15:00 | Barnsley v Portsmouth | D | 1-1 |
| England League 1 | 2018/12/11 19:45 | Portsmouth v Charlton | L | 1-2 |
| England League 1 | 2018/12/08 15:00 | Portsmouth v Southend | W | 2-0 |