Head to Head
| England - League 1 | 2019/11/05 19:45 | Portsmouth v Southend | L | 4-1 |
| 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 | 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 2 | 2020/10/03 14:00 | Crawley Town v Southend | D | 1-1 |
| England - League 2 | 2020/09/26 14:00 | Southend v Morecambe | L | 1-2 |
| England - League 2 | 2020/09/19 12:00 | Carlisle v Southend | L | 2-0 |
| England - League 2 | 2020/09/12 14:00 | Southend v Harrogate Town | L | 0-4 |
| England - EFL Trophy | 2020/09/08 16:30 | Southend v West Ham U21 | L | 1-3 |
| England - EFL Cup | 2020/09/05 12:00 | Gillingham v Southend | L | 1-0 |
| England - League 1 | 2020/03/07 15:00 | Southend v Bristol Rovers | W | 3-1 |
| England - League 1 | 2020/02/29 15:00 | Oxford Utd v Southend | L | 2-1 |
Away History
| England - League 1 | 2020/10/03 14:00 | Burton Albion v Portsmouth | W | 2-4 |
| England - League 1 | 2020/09/26 14:00 | Portsmouth v Wigan | L | 1-2 |
| England - League 1 | 2020/09/20 14:00 | Rochdale v Portsmouth | D | 0-0 |
| England - EFL Cup | 2020/09/17 18:45 | Brighton v Portsmouth | L | 4-0 |
| England - League 1 | 2020/09/12 14:00 | Portsmouth v Shrewsbury | D | 0-0 |
| England - EFL Trophy | 2020/09/08 18:00 | Portsmouth v Colchester | W | 2-0 |
| England - EFL Cup | 2020/08/29 14:00 | Stevenage v Portsmouth | W | 4-6 |
| England - League 1 | 2020/07/06 16:00 | Oxford Utd v Portsmouth | L | 6-5 |