[19] Gillingham 0-2 Southend [11] 2018-10-13 14:00
Weather: Windy Stadium: MEMS Priestfield Stadium Pitch: Excellent Round: 13
Referee: John Busby Home Manager: Stephen John Lovell Away Manager: Chris Powell
Head to Head
| England League 1 | 2018/04/02 14:00 | Southend v Gillingham | L | 4-0 |
| England EFL Trophy | 2017/08/29 18:45 | Gillingham v Southend | W | 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 | W | 2-1 |
| England EFL Cup | 2016/08/09 18:45 | Southend v Gillingham | W | 1-3 |
| England League 1 | 2016/08/06 14:00 | Southend v Gillingham | W | 1-3 |
| England League 1 | 2016/03/19 15:00 | Southend v Gillingham | D | 1-1 |
| England League 1 | 2015/10/24 14:00 | Gillingham v Southend | D | 1-1 |
Home History
| England EFL Trophy | 2018/10/09 18:45 | Gillingham v Tottenham U21 | L | 0-4 |
| England League 1 | 2018/10/06 14:00 | Portsmouth v Gillingham | W | 0-2 |
| England League 1 | 2018/09/29 14:00 | Shrewsbury v Gillingham | D | 2-2 |
| England League 1 | 2018/09/22 14:00 | Gillingham v Peterborough | L | 2-4 |
| England League 1 | 2018/09/15 14:00 | Rochdale v Gillingham | L | 3-0 |
| England League 1 | 2018/09/08 14:00 | Gillingham v AFC Wimbledon | L | 0-1 |
| England EFL Trophy | 2018/09/04 18:45 | Portsmouth v Gillingham | L | 4-0 |
| England League 1 | 2018/09/01 14:00 | Barnsley v Gillingham | L | 2-1 |
Away History
| England EFL Trophy | 2018/10/09 18:45 | Colchester v Southend | L | 2-0 |
| England League 1 | 2018/10/06 14:00 | Southend v Oxford Utd | D | 0-0 |
| England League 1 | 2018/10/02 18:45 | Burton Albion v Southend | W | 1-2 |
| England League 1 | 2018/09/29 14:00 | Wycombe v Southend | W | 2-3 |
| England League 1 | 2018/09/22 14:00 | Southend v Fleetwood Town | W | 1-0 |
| England League 1 | 2018/09/15 14:00 | Shrewsbury v Southend | L | 2-0 |
| England League 1 | 2018/09/08 14:00 | Southend v Peterborough | L | 2-3 |
| England EFL Trophy | 2018/09/04 18:45 | Southend v Cambridge Utd | W | 3-1 |