| RETURN TO LEAGUE LISTING | |||||||||||
| Year | Division | Home | Away | Date | Win | Draw | Loss | Gills Gls | Away Gls | ||
| 1919/20 | Southern League Div 1 | Gillingham | 0-1 | Southend United | 0 | 0 | 1 | 0 | 1 | ||
| Southern League Div 1 | Southend United | 0-1 | Gillingham | 1 | 0 | 0 | 1 | 0 | |||
| 1914/15 | Southern League Div 1 | Gillingham | 1-0 | Southend United | 1 | 0 | 0 | 1 | 0 | ||
| Southern League Div 1 | Southend United | 1-1 | Gillingham | 0 | 1 | 0 | 1 | 1 | |||
| 1913/14 | Southern League Div 1 | Gillingham | 4-2 | Southend United | 1 | 0 | 0 | 4 | 2 | ||
| Southern League Div 1 | Southend United | 2-3 | Gillingham | 1 | 0 | 0 | 3 | 2 | |||
| 1910/11 | Southern League Div 1 | Gillingham | 1-2 | Southend United | 0 | 0 | 1 | 1 | 2 | ||
| Southern League Div 1 | Southend United | 2-2 | Gillingham | 0 | 1 | 0 | 2 | 2 | |||
| 1909/10 | Southern League Div 1 | Gillingham | 5-0 | Southend United | 1 | 0 | 0 | 5 | 0 | ||
| Southern League Div 1 | Southend United | 3-0 | Gillingham | 0 | 0 | 1 | 0 | 3 | |||
| 1908/09 | Southern League Div 1 | Gillingham | 1-0 | Southend United | 1 | 0 | 0 | 1 | 0 | ||
| Southern League Div 1 | Southend United | 1-0 | Gillingham | 0 | 0 | 1 | 0 | 1 | |||