| Year | Award |
| 2021 | Porsche Parade: Newsletter Class II – Bluegrass Region Second Website Class II – Bluegrass Region Third Robert McClelland – Artwork 1st Place for Artwork and Honorable Mention Artwork |
| 2020 | Porsche Parade: Newsletter Class II – Bluegrass Region First Website Class II – Bluegrass Region Second |
| 2019 | Porsche Parade: Newsletter Class II – Bluegrass Region Third Website Class II – Bluegrass Region Third Robert McClelland – Artwork 1st Place award for his painting |
| 2019 | Keeneland Concours Paddock Challenge Trophy – The Bluegrass Region raised $2,698 for the Kentucky Children’s Hospital and took home the Paddock Challenge Trophy. |
| 2018 | Porsche Parade: Newsletter Class II – Bluegrass Region Second Website Class II – Bluegrass Region Second Key and Felicia Wilson – 1st Place in Group 1 Preparation in the Concours event, No. 1 in their Group, No. 1 in their Class, and were awarded the Stuttgart Level of Achievement Robert McClelland – Artwork 1st Place and 3rd Place awards for his paintings Phil Doty – 2nd Place in his Class for the Technical and Historical Quiz |
| 2018 | Keeneland Concours Paddock Challenge Trophy – Our Paddock raised the most and we took home the Paddock Challenge Trophy. We raised over $2500. |
| 2017 | Porsche Parade: Newsletter Class II – Bluegrass Region First Website Class II – Bluegrass Region Third |
| 2017 | Keeneland Concours Paddock Challenge Trophy – Hats off again to the Bluegrass Porsche Club for winning the Paddock Challenge Trophy for the tenth time in the thirteen times it has been contested! The $3,195 raised is the most in the past five years. |
| 2016 | Porsche Parade: Newsletter Class II – Bluegrass Region Second (tie) Website Class II – Bluegrass Region First |