The Convenors Outing Shield was presented to the League by Mr James Cowan (Clober G C) and first played for in 1988 where Mr Cowan promptly won it.
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Convenors Day Winners |
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| 1988 | J. Cowan - D. McIntyre | Clober |
| 1989 | H. Crawford - W. Paterson | Kilsyth Lennox |
| 1990 | J. Freel - J. Cuddihy | Craigmaddie |
| 1991 | C. McAteer - A. Emans | Palacerigg |
| 1992 | A. Haney - J. McKenna | Cawder |
| 1993 | J. Aitken - A. Barret | Kilsyth |
| 1994 | J. Montgomery - I. Jones | Dougalston |
| 1995 | T. Burke - J. Davidson | Windyhill |
| 1996 | J. Gallagher - J. Gallagher | Clydebank Overtoun |
| 1997 | T. Colvin - D. Urwin | Milngavie |
| 1998 | C. Pope - S. Russell | Renfrew |
| 1999 | M. Caven - B. Campbell | Dumbarton |
| 2000 | B. McMurray - J. Britton | Windyhill |
| 2001 | B. Bingham - W. Duncan | Kilsyth |
| 2002 | J. Payne - M. Green | Cardross |
| 2003 | D. McKinley - M. G. Watt | Dumbarton |
| 2004 | G. Smith - K. McHugh | Vale of Leven |
| 2005 | D.McAteer - J. Campbell | Dullatur |
| 2006 | P. McGlynn - L. McGlynn | Hayston |
| 2007 | P. McGlynn - L. McGlynn | Hayston |
| 2008 | S. Bolton - C. Fairhurst | Dougalston |
| 2009 | A. Bankier - W. Turner | Kilsyth |
| 2010 | J. Austin - P. Donnelly | Bearsden |
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