| Winter Division 4 League Champions |
| Year | Winner | Runner Up |
| 1987/88 | Croydon Squash Club | ??? |
| 1988/89 | ??? | ??? |
| 1989/90 | ??? | Dales 'A' |
| 1990/91 | ??? | ??? |
| 1991/92 | ??? | ??? |
| 1992/93 | ??? | ??? |
| 1993/94 | Royal Oak | Stag 'A' |
| 1994/95 | The Manor | Duke of Gloucester |
| 1995/96 | Blacksmiths Arms | Touch of Class |
| 1996/97 | ??? | ??? |
| 1997/98 | Legionaires | ??? |
| 1998/99 | The EPH | ??? |
| 1999/00 | British Legion | ??? |
| 2000/01 | ??? | ??? |
| 2001/02 | ??? | ??? |
| 2002/03 | ??? | ??? |
| 2003/04 | The Alexandra | The Royal Oak |
| 2004/05 | 2 Halfs | The S.A.S. |
| 2005/06 | Penge Trades | Coach & Horses |
| 2006/07 | Surrey 193's | The Imperials |
| 2007/08 | Elmer Cue Masters | Goodfellas |
| 2008/09 | Farley Big Potatoes | Beechtree |
| 2009/10 | Untouchables | The Wandering Dogs |
| 2010/11 | Penge Conservative Club | Surrey Arms |
| 2012/13 | Farley Small Potatoes | Cue Slammers |