Dan Garside kicked off this yearly competition between the School and the Old Southendians in the year 2000. Designed as a fun event which is played as two teams of 12 and 4BBB match play format. No handicap limits means golf players of all abilities are eligible and welcomed to play. A cup was donated by OSGC and since its inauguration it has been won thus:
| Year | Winner | Report |
|---|---|---|
| 2000 | OSGC | |
| 2001 | SHSB | |
| 2002 | SHSB | |
| 2003 | OSGC | |
| 2004 | OSGC | |
| 2005 | OSGC | |
| 2006 | OSGC | |
| 2007 | OSGC | |
| 2008 | SHSB | |
| 2009 | OSGC | |
| 2010 | SHSB | |
| 2011 | OSGC | |
| 2012 | SHSB | |
| 2013 | OSGC | |
| 2014 | SHSB | |
| 2015 | OSGC | |
| 2016 | OSGC | |
| 2017 | SHSB | |
| 2018 - 2025 | COVID-induced gap | |
| 2026 | OSGC | Report |
See the main OSGC page for contact details and general information on the Golf Circle, and for results of seasons past.
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