- 2018 Winners
- Sherri DuCharme-White from Medical College of Wisconsin won the use of a Jeep Wrangler for 2 years
- Colleen Hawley from Children’s Hospital of Wisconsin won a 2019 Harley-Davidson Iron 1200 Motorcycle
- Sarah Betthauser won $5,000 cash
- Kenneth Ward from Ruekert & Mielke won a Grand Geneva Resort & Spa getaway
- Richard Butler won the "Ultimate Milwaukee Entertainment Experience"
- Caroline Koch from ProHealth Care won a Cocoa Beach dream vacation
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- 2017 Winners
Christine Woloszyk from Capitas Financial won a New Chevy Traverse
Joyce Lutzow from Medical College of Wisconsin won a Harley-Davidson 2017 Street Rod 750
Lavar Matthews from ManpowerGroup won $5,000 cash
David Fularczyk from Children’s Hospital of Wisconsin won a Disney World vacation
Jeanne Decant from Boston Store won a $2,500 Boston Store grift card
Donna Slawson from Briohn Building won a Cocoa Beach vacation
Paul Cronce from Milsco won a Bucks Ultimate Fan Experience
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- 2016 Winners
Gregory Szeflinski from Harley-Davidson Motor Company won a New 2016 Chevy Malibu
Teng Yang from Rockwell Automation won a 2017 Harley-Davidson Softail Slim
Peter Castator from American Family Insurance Group won $5,000 cash
Nolberto Rosales from PPG Industries won the Milwaukee Bucks Ultimate Fan Experience
Mary Bartels from Swanson Elementary School won the Cocoa Beach Dream Vacation
Julie Risch from We Energies won a $2,500 Boston Store gift card
Cynthia Schaefer from the Marcus Center for the Performing Arts won a Disney World Vacation
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- 2015 Winners
Stacey Force, employee of ManpowerGroup, won the 2015 Chevy Cruze
Stephanie Warren, employee of Baird, won a 2015 Harley-Davidson Street 750 motorcycle
Stevan Keith, employee of City of Milwaukee, won the Cocoa Beach Dream Vacation.
Laura Dolnik, employee of Northwestern Mutual, won the $5000 spending cash
Cori Haugh, employee of Journal Media Group, won the $2500 Boston Store Gift Card.
Alan Cheslock, employee of Michael Best & Friedrich, won a Milwaukee Bucks Ultimate Fan Experience.
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- 2014 Winners
Fashion Fest prize: $2,500 to spend at Boston Store. Donated by Boston Store. A Cathedral Center employee who donated the prize to the Cathedral Center.
MKE Moola prize: A $5,000 cash. Donated by Patricia & Paul Purcell. Hamish Scrimgeour, Johnson Controls, Inc.
Hometown Hog prize: 2015 Dyna Low Rider® motorcycle. Donated by Harley-Davidson Motor Company. Jonathan Perez, ManpowerGroup
Cream City Cruze prize: A 2014 Chevy Cruze 4-Door Sedan. Donated by Johnson Controls, Inc. Thomas Conway, Johnson Controls, Inc.
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- 2013 Winners
Rafael Luna - Spring Break prize: Two tickets to the NCAA Final Four in North Texas, plus $3,000 for travel and expenses. Donated by Northwestern Mutual and Greg & Rhonda Oberland.
Kelly Flanagan - Winter Windfall prize: A $5,000 "Holiday Bonus" Mastercard® gift card to spend, share and save. Donated by BMO Harris Bank.
David Kennedy - Summer Cycle prize: 2014 Sportster SuperLow® XL883L motorcycle. Donated by Harley-Davidson Motor Company. (Transportation and set-up provided by Hal's Harley-Davidson. )
Linda Stewart - Autumn-obile prize: A NEW 2013 Ford Focus 4-Door Sedan SEL donated by Johnson Controls.
- 2012 Winners
Deirdre Carlisle - 2012 Ford Focus 4-Door Sedan SEL donated by Johnson Controls
Malisa Valeriano - 2013 Harley-Davidson Softail® Slim™ motorcycle donated by Harley-Davidson Motor Company
Thomas Sipin - Family trip for four to a Disney movie premiere including airfare, hotel, rental car and passes to Disneyland® Park donated by The Marcus Corporation and The Walt Disney Studios.
Joseph Cira -$2,000 shopping spree to Boston Store donated by Bon-Ton, Inc.
- 2011 Winners
Toula Hellauer - 2012 Ford Focus 5-Door Hatchback donated by Johnson Controls
Jane Eickhoff - 2012 Harley-Davidson® Blackline® Motorcycle and riding lessons
Robert Scheidt - Trip to Costa Rica: Airfare from MaxVantage, lodging donated by Rhonda and Tom Cardella, $500 in spending money in the form of a debit card donated by American Express, and a $500 pre-trip shopping spree in the form of a gift card for use at any Boston Store.
Brandon Gray - Apple iPad from Infoblox, one year of Time Warner hi-speed broadband, one year of digital cable and a cable iPad app from Time Warner Cable.