| Year | Champions | Runners-up | League Designation |
| 2004 | Perth XI | Crieff | Third Division |
| 2005 | Breadalbane XI | Strathmore XI | Third Division |
| 2006 | Strathmore XI | Kinross | Third Division |
| 2007 | Stathearn XI | Kinross | Third Division |
| 2008 | Kinross | Clackmannan XI | Third Division |
| 2009 | Glendelvine | Clackmannan XI | Third Division |
| 2010 | Almond Valley | Freuchie XI | Third Division |
| 2011 | St Andrews University Staff | Guthrie Park | Third Division |
| 2012 | Falkland XI | St Modans XI | Third Division |
| 2013-2020 | no competition | ||
| 2021 | Dalacraig | Strathmore XI | Recreation & Development Central |
| 2021 | Kismet | St Modans XI | Recreation & Development South |
With thanks to Alan Veitch