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Trail Blazers Trail Boss
| 2012 | Greg Peel |
| 2011 | Todd Rasmussen |
| 2010 | Jim Zito |
| 2009 | Ken Everett |
| 2008 | Greg Peel |
| 2007 | Brian Zimmerman |
| 2006 | Tony Mazzino |
| 2005 | Chris Galewood |
| 2004 | Mike Iwan |
| 2003 | Doug Bewley |
| 2002 |
Tom Kiffer |
| 2001 | Frank Pajcic |
| 2000 | Greg Peel |
| 1999 | Greg Peel |
| 1998 | Greg Peel |
| 1997 | Don Hollenbaugh |