| 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 |
| 2010-11 | Fountain Inn, Whiteparish | Butt of Ale |
| 2011-12 | Wilton Hotel, Wilton Road | Black Horse, West Tytherley |
| 2012-13 | Village Freehouse | George Inn, Shrewton |
| 2013-14 | Royal Oak A | Duck Inn A |
| 2014-15 | Duck Inn A | Lord Nelson, Winterslow |
| 2015-16 | Lions Head, Winterslow A | |
| 2016-17 | Duck Inn | |
| 2017-18 | The Lamb Inn, Nomansland | Black Horse, Hurdcott B |