| Year | Winner | Runner Up |
| 1992 | Castletown | ??? |
| 1993 | Castletown - (2) | ??? |
| 1994 | Castletown - (3) | ??? |
| 1995 | Castletown - (4) | ??? |
| 1996 | Castletown - (5) | ??? |
| 1997 | Castletown - (6) | ??? |
| 1998 | Castletown - (7) | ??? |
| 1999 | Castletown - (8) | ??? |
| 2000 | Castletown - (9) | ??? |
| 2001 | Castletown - (10) | Port St Mary |
| 2002 | Port St Mary | Peel Sunset |
| 2003 | Port St Mary - (2) | ??? |
| 2004 | Port St Mary - (3) | Castletown |
| 2005 | Castletown - (11) | North Ramsey |
| 2006 | Castletown - (12) | North Ramsey |
| 2007 | Castletown - (13) | North Ramsey |
| 2008 | Castletown - (14) | Nobles Mixed |
| 2009 | Castletown - (15) | Port St Mary |
| 2010 | North Ramsey | Castletown |
| 2011 | North Ramsey - (2) | Port St Mary |
| 2012 | North Ramsey - (3) | Castletown |
| 2013 | Mooragh Park - (4) | Port St Mary |
| 2014 | Port St Mary - (4) | Mooragh Park |
| 2015 | Port St Mary - (5) | South Ramsey |
| 2016 | Port St Mary - (6) | Castletown |
| 2017 | Port St Mary - (7) | South Ramsey |
| 2018 | Port St Mary - (8) | Castletown A |
| 2019 | Port St Mary - (9) | Castletown A |
| 2020 | Not ran - Covid-19 | |
| 2021 | Castletown A - (16) | Port St Mary A |
| 2022 | Castletown A - (17) | South Ramsey |
