The League champions are awarded the Peter Pitt Cup, which was donated in 1986 by the guv’nor of the Golden Lion. The runners-up initially received the Ernest Wright trophy; this was replaced by the Jessie Reynolds Memorial Cup.
Roll of honour
| Year | Winner | Runners-up |
| 2018/19 | Eagle Club | Red Arrows |
| 2017/18 | Flying Pockets | Jesters |
| 2016/17 | Plough Birds | Eagle Club |
| 2015/16 | Plough Birds | Eagle Club |
| 2014/15 | Eagle Club | Plough Birds |
| 2013/14 | Southend Conservative Club | Eagle Club |
| 2012/13 | Angels | Eagle Club |
| 2011/12 | Eagle Club | Jesters |
| 2010/11 | Angels | Eagle Club |
| 2009/10 | Wellstead Angels | Eagle Club |
| 2008/09 | Wellstead Angels | Eagle Club |
| 2007/08 | Westcliff British Legion | Wellstead Angels |
| 2006/07 | Westcliff British Legion | Southend Hospital Ladies |
| 2005/06 | Westcliff British Legion | Orchard Rooms |
| 2004/05 | Pool Shack | Southend Hospital Ladies |
| 2003/04 | Southend Hospital Ladies | Eagle Club |
| 2002/03 | Southend Hospital Ladies | Ship |
| 2001/02 | New Ship | Southend Hospital Ladies |
| 2000/01 | Ship | New Ship |
| 1999/2000 | Ship | Westcliff Club 98 |
| 1998/99 | Westcliff Club 98 | Southend Hospital Ladies |
| 1997/98 | Westcliff Club 98 | |
| 1996/97 | ||
| 1995/96 | Westcliff British Legion | Woodcutters |
| 1994/95 | Westcliff British Legion | Park |
| 1993/94 | Westcliff British Legion | Churchfields B |
| 1992/93 | Westcliff British Legion | Churchfields |
| 1991/92 | Flarepath | Woodcutters |
| 1990/91 | Churchfields | Hockley British Legion |
| 1989/90 | Maplin Club | Oakwood |
| 1988/89 | Oakwood | SFSSC B |
| 1987/88 | ||
| 1986/87 |
