The Ken Cummane Award has been donated by the Ken Cummane Foundation. Ken’s foundation has been the largest donator to the 2020 Fund. The award for the “Club Challenge Winner” goes to the club/organization who donates the most to the 2020 Fund throughout the year. A club can raise funds using any legal method they wish.
| History of Recipients | ||
| 2015/2016 | Not awarded | |
| 2014/2015 | Not awarded | |
| 2013/2014 | Not awarded | |
| 2012/2013 | Not awarded | |
| 2011/2012 | The High Game at the Arbutus Club | |
| 2010/2011 | Jesters Club | |
| 2009/2010 | The High Game at the Arbutus Club | |
| 2008/2009 | Halloween Open at the Bentall Centre Athletic Club | |
| 2007/2008 | The High Game at the Arbutus Club | |
| 2006/2007 | Halloween Open at the Bentall Centre Athletic Club | |