Who's won each championship the most, across league history. “Titles” is the total; the season shown is the last one they won it.
This season's champions are highlighted. From 2021–22 on, the A Flight playoff winner is the Club Champion, so this list stops in 2018–19 and no one is currently highlighted here.
| # | Player | Titles | Last Won |
|---|---|---|---|
| 1 | Kris Blonski | 8 | 2018-2019 |
| 2 | Russ Gray | 5 | 2018-2019 |
| 2 | Peter Child | 5 | 2015-2016 |
| 4 | Peter Kastrau | 4 | 2018-2019 |
| 4 | Mike Blonski | 4 | 2014-2015 |
| 4 | Alan Finlayson | 4 | 2014-2015 |
| 4 | Steve Dawe | 4 | 2012-2013 |
| 4 | Stephen Bernard | 4 | 2009-2010 |
| 9 | Derek Blonski | 3 | 2014-2015 |
| 9 | Chris Dion | 3 | 2014-2015 |
| 11 | Dan Baker | 2 | 2018-2019 |
| 11 | Candace Coe | 2 | 2016-2017 |
| 11 | Dave McDowell | 2 | 2010-2011 |
| 11 | Stan Shiraishi | 2 | 2010-2011 |
| 11 | Jan Bradley | 2 | 2002-2003 |
| 11 | Leah Dix | 2 | 2002-2003 |
| 11 | Heather Zucker | 2 | 2002-2003 |
| 18 | Kristi Ahokas | 1 | 2016-2017 |
| 18 | Roxane Dunmore | 1 | 2016-2017 |
| 18 | Lori Eddy | 1 | 2016-2017 |
| 18 | Graeme Reed | 1 | 2014-2015 |
| 18 | Dave Dean | 1 | 2011-2012 |
| 18 | Bob Neale | 1 | 2011-2012 |
| 18 | Brian Olson | 1 | 2011-2012 |
| 18 | Harry VanBoxmeer | 1 | 2011-2012 |
| 18 | Carl Lenarduzzi | 1 | 2010-2011 |
| 18 | Debbie Waugh | 1 | 2010-2011 |
| 18 | Dave Gingrich | 1 | 2006-2007 |
| 18 | Ray Book | 1 | 2005-2006 |
| 18 | Mike Howard | 1 | 2005-2006 |
| 18 | Rob Ireland | 1 | 2005-2006 |
| 18 | Leo Laviolette | 1 | 2005-2006 |
| 18 | Brian MacLennan | 1 | 2005-2006 |
| 18 | Mark Drummond | 1 | 2004-2005 |
| 18 | Roz Dion | 1 | 2003-2004 |
| 18 | Paul Peacock | 1 | 2003-2004 |
| 18 | Scott Stewart | 1 | 2003-2004 |
| 18 | Scott Liewellyn | 1 | 2002-2003 |
| 18 | Brad Gibson | 1 | 2001-2002 |
| 18 | Shannon Mackenzie | 1 | 2000-2001 |
| 18 | Murray Hann | 1 | 1999-2000 |
| 18 | Chuck Tomlinson | 1 | 1999-2000 |
| 18 | Rick Broadfoot | 1 | 1998-1999 |
| 18 | Doug Brunner | 1 | 1998-1999 |
| 18 | Dan Cole | 1 | 1998-1999 |
| 18 | Bill Paul | 1 | 1998-1999 |
| 18 | George Clifford | 1 | 1997-1998 |
| 18 | Ross Crocker | 1 | 1997-1998 |
| 18 | Vince Farkas | 1 | 1997-1998 |
| 18 | Eugene Steaffer | 1 | 1997-1998 |