The Miracle WorkerThe Dixie Swim Club
| Year | Category | Actor | Show |
|---|---|---|---|
| 2010 | Best Actress | Alexis Grundell | The Diary of Anne Frank |
| Best Actor | Brad T. Smith | The Diary of Anne Frank | |
| Best Supporting Actress | Jennifer Dixson | Tom Jones | |
| Best Supporting Actress | Lauren Hous | The Diary of Anne Frank | |
| Best Supporting Actor | Wilbur Bolton | The Diary of Anne Frank | |
| Cameo | Dwain Dixson | Tom Jones | |
| Backstage Award | Suzie Harmon | In Recognition and Appreciation of Dedication and Loyalty to Red Mask |
|
| Jean Lewis Scholarship | Ashley Mondisa | ||
| 2011 | Best Actress | Gracie Oliver | Romantic Fever |
| Best Actor | Mike Boedicker | Romantic Fever | |
| Best Supporting Actress | Nancy Henderson | Romantic Fever | |
| Best Supporting Actor | J. Edward DeVore | Laura | |
| Cameo | Lonnie Ford | Inherit the Wind | |
| Jean Lewis Scholarship | Michael Howard | ||
| 2012 | Best Actress | Nancy Henderson | All My Sons |
| Best Actor | Sonny Downing | All My Sons | |
| Best Supporting Actress | Sue Daugherty | Rumors | |
| Best Supporting Actor | Jim Crain | The Girls in 509 | |
| Cameo | Leslie Van Camp | All My Sons | |
| Jean Lewis Scholarship | Brooke Kuchefski | ||
| 2013 | Best Actress | Isabelle Peters | To Kill A Mockingbird |
| Best Actor | Andrew Peters | To Kill A Mockingbird | |
| Best Supporting Actress | Nancy Keener | To Kill A Mockingbird | |
| Best Supporting Actor | Brandon Parks | To Kill A Mockingbird | |
| Cameo | Vern Bergkoetter | To Kill A Mockingbird | |
| Jean Lewis Scholarship | Matthew Wilkie | ||
| 2014 | Best Actress | Ann Soderstrom | Sly Fox |
| Best Actor | Ted Sant | Sly Fox | |
| Best Supporting Actress | Mary Ann Laker | Sly Fox | |
| Best Supporting Actor | Darren Kilbury | Amateurs | |
| Cameo | Terry Hill | Sly Fox | |
| Jean Lewis Scholarship | Chad Myler | ||
| 2015 | Best Actress | Isabelle Peters | The Miracle Worker |
| Best Actor | Drake Taylor | The Miracle Worker | |
| Best Supporting Actress | Sue Daugherty | The Dixie Swim Club | |
| Best Supporting Actor | David Techtow | A Shot In the Dark | |
| Cameo | Andrew Cook | The Miracle Worker | |
| Jean Lewis Scholarship | Bailey Williams | ||
| 2016 | Best Actress | Jamie DeVore | A Streetcar Named Desire |
| Best Actor | Tyler Thompson | A Streetcar Named Desire | |
| Best Supporting Actress | Melanie Clark | Deathtrap | |
| Best Supporting Actor | Matt Hester | A Streetcar Named Desire | |
| Cameo | Jim Rogers | Deathtrap | |
| Jean Lewis Scholarship | Benjamin Lohrberg | ||
| 2017 | Best Actress | Brittany McDaniels | Proof |
| Best Actor | William L. Kephart | Ordinary People | |
| Best Supporting Actress | Isabelle Peters | Ordinary People | |
| Best Supporting Actor | Andrew Peters | Proof | |
| Cameo | Leslie VanCamp | The Musical Comedy Murders of 1940 | |
| Backstage Award | Jamey Coutant | In Recognition and Appreciation of Dedication and Loyalty to Red Mask | |
| Special Award | Kenny Harden | For longtime service to Red Mask | |
| Jean Lewis Scholarship | Katarina Blakeslee | ||
| 2018 | Best Actress | Leslie VanCamp | Rabbit Hole |
| Best Actor | Jeff Romig | Rabbit Hole | |
| Best Supporting Actress | Jenna Wilson | Rabbit Hole | |
| Best Supporting Actor | Jeff Romig | All Because of Agatha | |
| Cameo | Wilbur Bolton | All Because of Agatha | |
| Jean Lewis Scholarship | Molly Smith | ||
| 2019 | Best Actress | Barbara Whaling | Witness for the Prosecution |
| Best Actor | Marcus Provost | A Few Good Men | |
| Best Supporting Actress | Ann Soderstrom | Savannah Sipping Society | |
| Best Supporting Actor | Mark Learnard | Witness for the Prosecution | |
| Cameo | Gregory Duckett | Witness for the Prosecution | |
| Jean Lewis Scholarship | Katie Weston | ||