| Year | Large Business of the Year | Small Business of the Year | ||
| 2012 | 10 Barrel Brewing Company | Webfoot Painting Co | ||
| 2011 | Bend Research Inc | Donner Flower Shop | ||
| 2010 | Robberson Ford Sales | Integrated Eyecare | ||
| 2009 | Pepsi-Cola Bottling Co. of Bend | Jake’s Diner | ||
| 2008 | Pine Tavern Restaurant | Eastlake Framing | ||
| 2007 | Bend Garbage & Recycling | Sign Pro | ||
| 2006 | Miller Lumber Co | |||
| 2005 | Hooker Creek Companies, LLC | |||
| 2004 | Carlson Sign Co. | |||
| 2003 | The Center Orthopedic & Neurosurgical Care & Research | |||
| 2002 | Hap Taylor & Sons | |||
| 2001 | Les Schwab Tire Center – South | |||
| 2000 | The Athletic Club of Bend | |||
| 1999 | Kirby Nagelhout Construction | Newport Avenue Market | ||
| 1998 | Brooks Resources Corporation | Saxon’s Fine Jewelers | ||
| 1997 | Pacific Power | BBT Architects | ||
| 1996 | Deschutes Brewery | Barrett Business Services | ||
| 1995 | Mt. Bachelor | Combined Communications | ||
| 1994 | The Riverhouse | Every Idea | ||
| 1993 | The Bulletin | Royal Blend | ||
| 1992 | Bank of the Cascades | Mirror Pond Cleaners | ||
| 1991 | St Charles | |||
| 1990 | Pepsi Cola Bottling Co of Bend and Bend Mill Work | |||
*Years 1990 & 1991 and 2000-2006 Business of the Year was awarded to one business
Citizen of the Year
2012 Jim Lussier
2011 Oran Teater
2010 Paul Reynolds
2009 Taffy Gleason
2008 Les & Judy Alford
2007 Clella Thomas
2006 William & Trish Smith
2005 Connie Worrell-Druliner
2004 Ron Carver & Jim Peterson
2003 H.M. Kemple
2002 Mike Hollem & Sue Hollem
2001 Barbara Schenck
2000 Patricia Moss
1999 Gary Fish
1998 Jim Crowell
1997 Loren Irving
1996 Craig Moore
1995 John Larkin
1994 Greg Cushman
1993 Dennis Maloney
1992 Judy Duncan
1991 Stuart Garrett
1990 Eric Alexander
Organization of the Year
2012 Healthy Beginnings
2011 Saving Grace
2010 Family Access Network (FAN)
2009 Central Oregon Resources for Independent Living (CORIL)
2008 Deschutes Children’s Foundation
2007 Bethlehem Inn Homeless Shelter
2006 MountainStar Family Relief Nursery







