| Winter Division 5 League Champions |
| Year | Winner | Runner Up |
| 1982/83 | ??? | Crescent A |
| 1983/84 | ??? | ??? |
| 1984/85 | ??? | ??? |
| 1985/86 | ??? | ??? |
| 1986/87 | Croydon Squash Club | ??? |
| 1987/88 | ??? | ??? |
| 1988/89 | ??? | Dales 'A' |
| 1989/90 | ??? | ??? |
| 1990/91 | ??? | ??? |
| 1991/92 | ??? | ??? |
| 1992/93 | ??? | ??? |
| 1993/94 | Leslie Eagles | The Railway |
| 1994/95 | The Fish | Bromley Cue Sports 'A' |
| 1995/96 | Royal Oak | Rose and Crown |
| 1996/97 | ??? | ??? |
| 1997/98 | The EPH | ??? |
| 1998/99 | ??? | ??? |
| 1999/00 | ??? | ??? |
| 2000/01 | ??? | ??? |
| 2001/02 | ??? | ??? |
| 2002/03 | ??? | ??? |
| 2003/04 | Hotshots | Pond Potters |
| 2004/05 | New Circle Hounds | Coach & Horses |
| 2005/06 | The New Imperials | The Folly |
| 2006/07 | Jolly Sailor | Chopper Squad |
| 2007/08 | Penge Trades | Beechtree Crowns |
| 2008/09 | Farley Untouchables | The Oak |
| 2009/10 | The Crown Balls | Forestdale Arms |
| 2010/11 | William The Conquerers | Another View |