Encouragement Award
Awarded to an orienteer who makes efforts to encourage other orienteers by both personal efforts and example. Also known as the Cox's Cup as it was generously donated by Bryony and Tim Cox of Garingal.
| 2023 | Selwyn Sweeney | Western & Hills |
| 2022 | Richard Pattison | Bennelong |
| 2021 | Barbara Dawson | Garingal |
| 2020 | Barry Hanlon and Janet Morris | Western & Hills |
| 2019 | Ian Jessup | Garingal/ONSW |
| 2018 | Maurice Anker | Northern Tablelands |
| 2017 | Jean and Basil Baldwin | Goldseekers |
| 2016 | Helen O'Callaghan | Bush n Beach |
| 2015 | Paula Shingler | Big Foot |
| 2014 | Janet Morris | Western & Hills |
| 2013 | Bruce Meder | Bush n Beach |
| 2012 | Greg Bacon | Newcastle |
| 2011 | John Oliver | Waggaroos |
| 2010 | Carolyn Rigby | Newcastle |
| 2009 | Geoff Todkill | Newcastle |
| 2008 | Karen Hagan | Western Plains |
| 2007 | Barbara Hill | Garingal |
| 2006 | Ross Barr | Garingal |
| 2005 | Colin Price | Central Coast |
| 2004 | Barbara Hill | Garingal |
| 2003 | Brian Johnson | Garingal |
| 2002 | Ian Miller | Western & Hills |
| 2001 | Lynn Dabbs | Western & Hills |
| 2000 | Ken Sinclair | |
| 1999 | Dot Denham | |
| 1998 | Ian Warlters | |
| 1997 | Graham Galbraith | Bennelong Northside |
| 1996 | Lyn Malmgron | Southern Highlands |
| 1995 | Neil Lowndes | |
| 1994 | Arthur Durham | Uringa |
