North District Championship – Association Cup
| Year | Name | Club | Venue |
| 2019 | M.Schinkel | Royal Dornoch | Brora |
| 2018 | K.Godsman | Moray | Tain |
| 2017 | B.Fotheringham | Forres | Nairn Dunbar |
| 2016 | B.Fotheringham | The Nain | Elgin |
| 2015 | B.Fotheringham | Inverness | Brora |
| 2014 | D.Thorburn | Tain | Moray |
| 2013 | K.Godsman | Moray | Royal Dornoch |
| 2012 | B.Thomson | The Nairn | Inverness |
| 2011 | B.Fotheringham | Inverness | Elgin |
| 2010 | N.McWilliam | Elgin | Loch Ness |
| 2009 | J.Treasurer | Inverness | Thurso |
| 2008 | B.Fotheringham | Forres | Forres |
| 2007 | D.J.Stewart | Grantown-on-Spey | Tain |
| 2006 | D.J.Stewart | Grantown-on-Spey | Moray |
| 2005 | M.MacDonald | Fortrose & Rosemarkie | Inverness |
| 2004 | M.Ross | Elgin | Elgin |
| 2003 | S.McIntosh | Torvean | Loch Ness |
| 2002 | Royal Dornoch | Tain | |
| 2001 | N.G.Pears | Nairn Dunbar | Nairn Dunbar |
| 2000 | J.S.D.Campbell | Grantown-on-Spey | Moray |
| 1999 | G.Hay | Nairn | Inverness |
| 1998 | R.Sheils | Moray | Boat of Garten |
| 1997 | S.Wilson | Royal Dornoch | Golspie |
| 1996 | S.McIntosh | Muir of Ord | Tain |
| 1995 | N.D.Hampton | Nairn | Moray |
| 1994 | S.McIntosh | Muir of Ord | Inverness |
| 1993 | S.Leith | Moray | Royal Dornoch |
| 1992 | S.McIntosh | Muir of Ord | Elgin |
| 1991 | N.D.Hampton | Fortrose & Rosemarkie | Brora |
| 1990 | B.Wann | Nairn | Tain |
| 1989 | J.Miller | Brora | Nairn |
| 1988 | J.Miller | Brora | Fortrose & Rosemarkie |
| 1987 | G.Bain | Grantown-on-Spey | Nairn Dunbar |
| 1986 | N.S.Grant | Moray | Forres |
| 1985 | J.S.Macdonald | Elgin | Tain |
| 1984 | N.S.Grant | Elgin | Elgin |
