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owner
of the Standing Stones Hotel. The first season saw 11 teams (Barony, Braes,
Ferry Inn 1, Ferry Inn 2, Legion 1, Legion 2, Scorrabrae, Smithfield,
Standing Stones 1, Standing Stones 2 and Stromness Hotel) compete for the
title and it was the Standing Stones 1 who lifted the trophy.
| Year | Winners | Year | Winners | MOST TIMES WINNERS | | 1983-84 | Standing Stones | 2005-06 | Golf Club | Golf Club | 14 | | 1984-85 | Standing Stones | 2006-07 | Barony | Smithfield | 7 | | 1985-86 | Legion 1 | 2007-08 | Legion 1 | Legion | 7 | | 1986-87 | Standing Stones 1 | 2008-09 | Smithfield | Ferry Inn | 4 | | 1987-88 | Standing Stones 1 | 2009-10 | Barony | Standing Stones | 4 | | 1988-89 | Golf Club | 2010-11 | Legion 1 | Mistra | 2 | | 1989-90 | Legion 1 | 2011-12 | Legion 1 | Barony | 2 | | 1990-91 | Golf Club 1 | 2012-13 | Legion 1 | Stromness | 1 | | 1991-92 | Golf Club | 2013-14 | Pomona | Pomona | 1 | | 1992-93 | Smithfield | 2014-15 | Smithfield | | | | 1993-94 | Stromness 1 | 2015-16 | Smithfield | MOST WINS (players) | | 1994-95 | Golf Club 1 | 2016-17 | Mistra | Angus Sutherland | 14 | | 1995-96 | Golf Club 1 | 2017-18 | Golf Club | Davie Keldie | 13 | | 1996-97 | Golf Club | 2018-19 | Smithfield | Eric Sutherland | 12 | | 1997-98 | Golf Club | 2019-20 | Golf Club | | | | 1998-99 | Golf Club | 2020-21 | NOT PLAYED COVID | | | | 1999-00 | Mistra | 2021-22 | Smithfield | | | | 2000-01 | Golf Club | 2022-23 | Smithfield | | | | 2001-02 | Ferry Inn 1 | 2023-24 | Golf Club | | | | 2002-03 | Ferry Inn 1 | 2024-25 | Golf Club | | | | 2003-04 | Ferry Inn 1 | 2025-26 | Legion | | | | 2004-05 | Ferry Inn 1 | | | | |
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