| Year | Champions | Runners-up | League Designation |
| 1999 | Arbroath XI | Norwood | Second Division |
| 2000 | Kinloch | Strathmore XI | Second Division |
| 2001 | No Competition | ||
| 2002 | Perth | Forthill XI | Second Division |
| 2003 | Forthill XI | Arbroath XI | Second Division |
| 2004 | Coupar Angus | Breadalbane | Second Division |
| 2005 | Arbroath XI | Crieff | Second Division |
| 2006 | Forthill XI | Crieff | Second Division |
| 2007 | Northern | Montrose | Second Division |
| 2008 | Montrose | Rossie Priory XI | Second Division |
| 2009 | Kinross | Norwood | Second Division |
| 2010 | Gordonians | Mayfield | Second Division |
| 2011 | Arbroath XI | Dalnacraig | Second Division |
| 2012 | St Andrews University Staff | Strathmore XI | Second Division |
| 2013 | St Andrews University Staff | Perth Doo’Cot XI | Second Division South |
| 2013 | Arbroath XI | Strathmore XI | Second Division North |
| 2014 | Breadalbane | Alloa XI | Second Division South |
| 2014 | Arbroath XI | Strathmore XI | Second Division North |
| 2015 | Falkland XI | St Modans XI | Second Division South |
| 2015 | Arbroath XI | Strathmore XI | Second Division North |
| 2016 | Dunnikier | Glenrothes XI | Recreation & Development East |
| 2016 | Arbroath XI | Mannofield XI | Recreation & Development North |
| 2016 | Perth Doo’Cot 3rd XI | Doune | Recreation & Development West |
| 2017 | Strathmore XI | Arbroath XI | Recreation & Development Central |
| 2017 | Kismet | Freuchie Third XI | Recreation & Development East |
| 2017 | Stoneywood Dyce XI | Mannofield XI | Recreation & Development North |
| 2017 | Comrie | Doune | Recreation & Development West |
| 2018 | Meigle XI | Strathmore XI | Recreation & Development Central |
| 2018 | Kismet | Dunnikier | Recreation & Development East |
| 2018 | Mannofield XI | Aberdeen GSFP XI | Recreation & Development North |
| 2018 | Breadalbane | Stirling County XI | Recreation & Development West |
| 2019 | Brechin Buccaneers | Strathmore XI | Recreation & Development Central |
| 2019 | Freuchie Third XI | Dunfermline Wanderers | Recreation & Development East |
| 2019 | Mannofield XI | Aberdeen GSFP XI | Recreation & Development North |
| 2019 | St Modans XI | Kinross-shire | Recreation & Development West |
| 2020 | no competition | ||
| 2021 | Meigle Second XI | Callander | Second Division |
| 2022 | St Modan’s | Kinloch Second XI | Second Division |
| 2023 | Kinloch | Glenrothes | Second Division |
Alan Veitch, Neil Leitch