[12] Southend 2-0 Gillingham [18] 2019-01-01 15:00
Weather: Cold Stadium: Roots Hall Pitch: Good Round: 26
Referee: Keith Stroud Home Manager: Chris Powell Away Manager: Stephen John Lovell
Head to Head
| England League 1 | 2018/10/13 14:00 | Gillingham v Southend | W | 0-2 |
| England League 1 | 2018/04/02 14:00 | Southend v Gillingham | W | 4-0 |
| England EFL Trophy | 2017/08/29 18:45 | Gillingham v Southend | L | 2-1 |
| England League 1 | 2017/08/26 14:00 | Gillingham v Southend | D | 3-3 |
| England League 1 | 2017/02/25 15:00 | Gillingham v Southend | L | 2-1 |
| England EFL Cup | 2016/08/09 18:45 | Southend v Gillingham | L | 1-3 |
| England League 1 | 2016/08/06 14:00 | Southend v Gillingham | L | 1-3 |
| England League 1 | 2016/03/19 15:00 | Southend v Gillingham | D | 1-1 |
Home History
| 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 |
| England League 1 | 2018/11/27 19:45 | Southend v Scunthorpe | W | 2-0 |
Away History
| England League 1 | 2018/12/29 15:00 | Gillingham v Doncaster | L | 1-3 |
| England League 1 | 2018/12/26 13:00 | Gillingham v Portsmouth | W | 2-0 |
| England League 1 | 2018/12/22 15:00 | Charlton v Gillingham | L | 2-0 |
| England League 1 | 2018/12/15 15:00 | Gillingham v Wycombe | D | 2-2 |
| England League 1 | 2018/12/08 15:00 | Scunthorpe v Gillingham | W | 0-2 |
| England FA Cup | 2018/12/02 14:00 | Slough v Gillingham | W | 0-1 |
| England League 1 | 2018/11/27 19:45 | Bristol Rovers v Gillingham | W | 1-2 |
| England League 1 | 2018/11/24 15:00 | Gillingham v Luton | L | 1-3 |