| Category | Place | Organization |
| 2012 | ||
| Schools & School Clubs | 1st | |
| 2nd | ||
| 3rd | ||
| Organizations, Clubs & Scouts | 1st | |
| 2nd | ||
| 3rd | ||
| Churches & Church Organizations | 1st | |
| 2nd | ||
| 3rd | ||
| Government & Municipalities | 1st | |
| 2nd | ||
| 3rd | ||
| Commercial | 1st | |
| 2nd | ||
| 3rd | ||
| Most Effective Use of Lighting | 1st | |
| 2nd | ||
| 3rd | ||
| Best Over All – Highest Total Points |
| Category | Place | Organization |
| 2011 | ||
| Schools & School Clubs | 1st | Maximilian Montesorri Academy |
| 2nd | Daymar College | |
| 3rd | Apollo Future Farmers of America | |
| Organizations, Clubs & Scouts | 1st | Owensboro Roller Skaters Club |
| 2nd | Girl Scout Troop 1016 | |
| 3rd | Right to Life Owensboro | |
| Churches & Church Organizations | 1st | Saints Joesph and Paul Catholic Church |
| 2nd | Grove Kids of Pleasant Grove Baptist Church | |
| 3rd | First General Baptist Church | |
| Government & Municipalities | 1st | Owensboro Street Department |
| 2nd | City of Hartford Recycling | |
| 3rd | Owensboro Sanitation | |
| Commercial | 1st | Cheri’s Creations |
| 2nd | Trunnell’s Farm Market | |
| 3rd | Owensboro Parent Magazine | |
| Most Effective Use of Lighting | 1st | Owensboro Street Department |
| 2nd | Saints Joesph and Paul Catholic Church | |
| 3rd | Cheri’s Creations | |
| Best Over All – Highest Total Points | Owensboro Street Department |
| 2010 | ||
| Schools & School Clubs | 1st | Owensboro Community & Technical College Art Club |
| 2nd | Maximilian Montesorri Academy | |
| 3rd | Daymar College | |
| Organizations, Clubs & Scouts | 1st | Sutton Elementary Girl Scouts |
| 2nd | Owensboro Roller States Club | |
| 3rd | Southern Oaks Elementary Girl Scouts | |
| Churches & Church Organizations | 1st | First General Baptist Church |
| 2nd | Crosspoint Baptist Church | |
| 3rd | Grove’s Kids of Pleasant Grove Baptist Church | |
| Government & Municipalities | 1st | Owensboro Street Department |
| 2nd | City of Hartford Recycling | |
| 3rd | Owensboro Sanitation | |
| Commercial | 1st | Wright Implement |
| 2nd | Cheri’s Creations | |
| 3rd | Kenergy | |
| Most Effective Use of Lighting | 1st | Owensboro Street Department |
| 2nd | Owensboro Sanitation Department | |
| 2009 | ||
| Schools & School Clubs | 1st | Apollo High School Habitat for Humanity |
| 2nd | Majesty Academy | |
| 3rd | West Louisville Elementary School | |
| Organizations, Clubs & Scouts | 1st | Cub Scout Pack 611 |
| 2nd | Kentucky Fastpitch Mustangs | |
| 3rd | Community Solutions for Substance Abuse | |
| Churches & Church Organizations | 1st | First General Baptist Church |
| 2nd | “Grove Kids” from Pleasant Grove Baptist | |
| 3rd | Yelvington Baptist Church Youth Group | |
| Government & Municipalities | 1st | Owensboro Street Department |
| 2nd | Owensboro Sanitation Department | |
| 3rd | Owensboro Transit Trolley | |
| Commercial | 1st | Wright Implement |
| 2nd | Home Depot | |
| 3rd | Checkered Flag Speedway | |
| Most Effective Use of Lighting | 1st | Owensboro Street Department |
| 2nd | Owensboro Sanitation Department | |
| 2008 | ||
| Schools & School Clubs | 1st | Majesty Academy |
| 2nd | Owensboro Middle School Cheerleaders | |
| 3rd | Kentucky Wesleyan College | |
| Organizations, Clubs & Scouts | 1st | Friends |
| 2nd | Kentucky Fastpitch Mustangs | |
| 3rd | Owensboro Lions Club | |
| Churches & Church Organizations | 1st | Pleasant Grove Baptist Church |
| 2nd | Yelvington Baptist Church Youth Group | |
| 3rd | ||
| Government & Municipalities | 1st | Owensboro Street Department |
| 2nd | City of Owensboro Facilities Maintenance Department & Neighborhood Aliances | |
| 3rd | Owensboro Sanitation Department | |
| Commercial | 1st | Skates Alive |
| 2nd | First Impressions Lawn Service | |
| 3rd | Home Depot | |
| Most Effective Use of Lighting | 1st | Majesty Academy |
| 2nd | Owensboro Street Department | |
| 2007 | ||
| Schools & School Clubs | 1st | Majesty Academy |
| 2nd | Owensboro Community & Technical College Art Club | |
| 3rd | Apollo High School Habitat Chapter | |
| Organizations, Clubs & Scouts | 1st | Girl Scouts Troup 27 |
| 2nd | The Alma Randolph Charitable Foundation | |
| 3rd | Ensor Masonic Lodge 729 and Goel Chapter 104 | |
| Churches & Church Organizations | 1st | Settle Memorial United Methodist Church |
| 2nd | First Free Will Baptist Church | |
| 3rd | Yelvington Baptist Church | |
| Government & Municipalities | 1st | Owensboro Street Department |
| 2nd | Owensboro Sanitation Department | |
| 3rd | Daviess County Detention Center | |
| Commercial | 1st | U. S. Bank Home Mortgage |
| 2nd | Home Reality | |
| 3rd | Maurice Pools and Spas | |
| Most Effective Use of Lighting | 1st | Majesty Academy |
| 2nd | Owensboro Sanitation Department | |
| Category | Place | Organization |
| 2006 | ||
| Schools & School Clubs | 1st | Owensboro Community & Technical College Art Club |
| 2nd | Majesty Academy | |
| 3rd | Apollo High School Habitat Chapter | |
| Organizations, Clubs & Scouts | 1st | Cub Scout Pack 611 |
| 2nd | Girl Scout Troop 1123 | |
| 3rd | Girl Scout Troop 942 | |
| Churches & Church Organizations | 1st | Owensboro Christian Church |
| 2nd | Glenmary Sisters | |
| 3rd | Masonville United Methodist Church | |
| Government & Municipalities | 1st | Owensboro Street & Sanitation Department |
| 2nd | Owensboro Riverport Authority | |
| 3rd | Daviess County Detention Center | |
| Commercial | 1st | DNJ Auto Parts & Sales |
| 2nd | Unilever Foods | |
| 3rd | U. S. Bank | |
| Most Effective Use of Lighting | 1st | Owensboro Street & Sanitation Department |
| 2nd | Cub Scout Pack 611 | |
| 2005 | ||
| Schools & School Clubs | 1st | Owensboro Community & Technical College
Student Government Association and Art Club
|
| 2nd | Kentucky Wesleyan Collage Purple Haze Dance Team | |
| 3rd | Triplett School | |
| Organizations, Clubs & Scouts | 1st | St. Pius Cub Scout Pack 120 |
| 2nd | Cub Scout Pack 611 | |
| 3rd | Red Hat Gypsies | |
| Churches & Church Organizations | 1st | Owensboro Christian Church |
| 2nd | Masonville United Methodist Church | |
| 3rd | Settle Memorial United Methodist Church | |
| Government & Municipalities | 1st | Owensboro Sanitation Department |
| 2nd | Owensboro-Daviess County Regional Airport | |
| 3rd | Owensboro Riverport Authority | |
| Commercial | 1st | DNJ Auto Parts |
| 2nd | Unilever Foods | |
| 3rd | E-Z Buy Auto Sales | |
| Most Effective Use of Lighting | 1st | E-Z Buy Auto Sales |
| 2nd | Owensboro Sanitation Department | |
| Highest Scoring Float | St. Pius Cub Scout Pack 120 |
| 2004 | ||
| Schools & School Clubs | 1st | Triplett School |
| 2nd | Daviess County High School Pantherettes | |
| 3rd | Owensboro Public Schools Transportation | |
| Organizations, Clubs & Scouts | 1st | Cub Scout Pack 611 |
| 2nd | Cub Scout Pack 225 | |
| 3rd | International Bluegrass Music Museum | |
| Churches & Church Organizations | 1st | St. Vincent de Paul |
| 2nd | Mary Kendall Campus | |
| 3rd | Apollo Heights Baptist Church | |
| Government & Municipalities | 1st | Owensboro Sanitation Department |
| 2nd | Owensboro Riverport Authority | |
| 3rd | Green River District Home Health | |
| Commercial | 1st | U.S. Bank |
| 2nd | Perfection Lawn Care | |
| 3rd | DNJ Auto Parts | |
| Most Effective Use of Lighting | 1st | Owensboro Sanitation Department |
| 2nd | Cub Scout Pack 611 | |
| 2003 | ||
| Schools & School Clubs | 1st | Apollo High School Habitat Club |
| 2nd | Owensboro Community & Technical College | |
| 3rd | Apollo FFA | |
| Organizations, Clubs & Scouts | 1st | Girl Scout Troop 690/263 |
| 2nd | Quest for Kids | |
| 3rd | Girl Scout Troop 453 | |
| Churches & Church Organizations | 1st | New Hope United Church of Christ |
| 2nd | Glenmary Missions | |
| 3rd | Church Alive | |
| Government & Municipalities | 1st | Owensboro Sanitation Department |
| 2nd | Green River Area Development District | |
| 3rd | Owensboro Riverport Authority | |
| Commercial | 1st | R. C. Bratcher Welding |
| 2nd | U.S. Bank | |
| Tied | 3rd | Owensboro Medical Health Systems |
| Tied | 3rd | Windy Hollow Speedway |
| Most Effective Use of Lighting | 1st | Austin Moore/Trace Stuart Racing |
| 2nd | R.C. Bratcher | |
| 3rd | Green River Area Development District | |
| 2002 | ||
| Schools | 1st | CVMS Dance Team |
| 2nd | Sorgho P-1 | |
| 3rd | OCC | |
| 4th | DCMS Beta Club | |
| Clubs & Organizations | 1st | Parents Troop 1812 |
| 2nd | Carmel Home | |
| Tied | 3rd | Quest for Kids, Inc. |
| Tied | 3rd | GRADD |
| 4th | Jr. Girl Scouts #438 | |
| Most Effective Use of Lighting | 1st | R. C. Bratcher |
| 2nd | Sorgho P-1 | |
| 3rd | CVMS Vikette Dance Team | |
| 4th | Quest for Kids, Inc. | |
| Commercial Category | 1st | R. C. Bratcher |
| 2nd | Executive Inn | |
| 3rd | OMHS |
| 2001 | ||
| Schools | 1st | Owensboro Community College |
| 2nd | College View Middle School 8th Grade Viking Cheerleaders | |
| 3rd | Catholic Home School | |
| Clubs & Organizations | 1st | Cliff Hagan Boys & Girls Club & Owensboro Housing Authority |
| 2nd | Foster Home/Department Community Based Services | |
| 3rd | Apollo Heights Baptist/Apollo Area Alliance | |
| Most Effective Use of Lighting | 1st | Cliff Hagan Boys & Girls Club & Owensboro Housing Authority |
| 2nd | Executive Inn Rivermont | |
| 3rd | Foster Home/Department Community Based Services | |
| Commercial Category | 1st | Ohio Valley 2-way Radio, Inc. |
| 2nd | Owensboro Mercy Health System Home Care | |
| 3rd | Wendell Foster’s Campus for Developmental Disabilities | |
| 2000 | ||
| Schools | 1st | Catholic Home Schools |
| 2nd | Hager Pre-School | |
| 3rd | OCMS Cheerleaders | |
| Clubs & Organizations | 1st | New Life Worship |
| 2nd | Carmel Home | |
| 3rd | Apollo Heights Baptist Church | |
| Most Effective Use of Lighting | 1st | Target |
| 2nd | Catholic Home Schools | |
| 3rd | New Life Worship |