[1] Portsmouth 2-0 Southend [14] 2018-12-08 15:00
Weather: Heavy Rain Stadium: Fratton Park Pitch: Good Round: 21
Referee: Lee Collins Home Manager: Kenneth Francis Jackett Away Manager: Chris Powell
Head to Head
| 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 | 2018/12/04 19:45 | Portsmouth v Arsenal U21 | W | 2-1 |
| England FA Cup | 2018/12/02 14:00 | Rochdale v Portsmouth | W | 0-1 |
| England League 1 | 2018/11/27 19:45 | Portsmouth v Walsall | W | 2-0 |
| England League 1 | 2018/11/24 15:00 | Scunthorpe v Portsmouth | W | 1-2 |
| England EFL Trophy | 2018/11/13 19:45 | Portsmouth v Tottenham U21 | W | 3-2 |
| England FA Cup | 2018/11/10 12:30 | Maidenhead Utd v Portsmouth | W | 0-4 |
| England League 1 | 2018/11/03 15:00 | Bradford v Portsmouth | W | 0-1 |
| England League 1 | 2018/10/27 14:00 | Accrington Stanley v Portsmouth | D | 1-1 |
Away History
| 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 |
| England League 1 | 2018/11/27 19:45 | Southend v Scunthorpe | W | 2-0 |
| England League 1 | 2018/11/24 15:00 | AFC Wimbledon v Southend | L | 2-1 |
| England FA Cup | 2018/11/20 19:45 | Crawley Town v Southend | W | 2-6 |
| England League 1 | 2018/11/17 15:00 | Southend v Blackpool | L | 1-2 |
| England EFL Trophy | 2018/11/14 19:45 | Southend v Southampton U21 | W | 3-0 |
| England FA Cup | 2018/11/10 15:00 | Southend v Crawley Town | D | 1-1 |