| Year | Winner | Runner-Up |
|---|---|---|
| 1998-99 | Railway Tavern | Lions Head 'A' |
| 1999-00 | Six Bells | White Horse, Quidhampton |
| 2000-01 | Silver Plough, Pitton | Royal George 'A' |
| 2001-02 | Black Horse, Hurdcott 'B' | Old Inn, Woodfalls 'A' |
| 2002-03 | Hogs Head | Parish Lantern, Whiteparish |
| 2003-04 | Black Horse, Hurdcott 'B' | Royal George 'A' |
| 2005-06 | Silver Plough, Pitton | Royal George 'A' |
| 2006-07 | Kings Arms, Fisherton St 'B' | Duck Inn, Laverstock |
| 2007-08 | Lamb Inn, Nomansland | Royal Oak |
| 2009-10 | Lions Head, Winterslow | Cuckoo Inn, Hamptworth 'B' |