| Year | Winner | Runner-Up |
| 2020-21 | No season | No season |
| 2019-20 | Season Void | Season Void |
| 2018-19 | Greg Alexander | David Jack |
| 2017-18 | Graham Dunbar | Paddy Nicoll |
| 2016-17 | Gary McLeish | Mark Donald |
| 2015-16 | David Jack | Paddy Nicoll |
| 2014-15 | No Competition | |
| 2013-14 | No Competition | |
| 2012-13 | Paddy Nicoll | Ian Anderson |
| 2011-12 | David Jack | Stuart Smith |
