| Year | Category | Actor | Show |
|---|---|---|---|
| 2000 | Best Actress | Jan Marken | Never Too Late |
| Best Actor | Joe Sermersheim | Of Mice and Men | |
| Best Supporting Actress | Bev Nees | I Bet Your Life | |
| Best Supporting Actor | Sonny Downing | Of Mice and Men | |
| Cameo | Joe Sermersheim | Never Too Late | |
| Backstage Award | Sheryl Walsh | For Set Building and Stage Managing | |
| Jean Lewis Scholarship | Nathan Marken | ||
| 2001 | Best Actress | Jerilyn Hempel | Sylvia |
| Best Actor | Dave Downing | Sylvia | |
| Best Actor | John Scott | The Last Night of Ballyhoo | |
| Best Supporting Actress | Gaye Garner | Sylvia | |
| Best Supporting Actor | Greg Williams | The Last Night of Ballyhoo | |
| Backstage Award | John Lashbrook | For work with Childrens Theater, Set Building, and Ambassador for the Organization | |
| Jean Lewis Scholarship | Jennifer Lee | ||
| 2002 | Best Actress | Jennifer Dixson | Breaking Legs |
| Best Actress | Jennifer Dixson | Belles | |
| Best Actor | Bob Scott | I Hate Hamlet | |
| Best Supporting Actress | Mary Ann Laker | Belles | |
| Best Supporting Actor | Joe Sermersheim | Breaking Legs | |
| Jean Lewis Scholarship | Rebecca Cravens | ||
| 2003 | Best Actress | Sharon Tipsword | The Cemetery Club |
| Best Actor | Ed DeVore | One Flew Over the Cuckoo's Nest | |
| Best Supporting Actress | Jamie DeVore | George Washington Slept Here | |
| Best Supporting Actor | Jim Wolfe | One Flew Over the Cuckoo's Nest | |
| Cameo | Chuck Minne | One Flew Over the Cuckoo's Nest | |
| Backstage | Sue Harden | In Recognition and Appreciation of Dedication and Loyalty to Red Mask | |
| Jean Lewis Scholarship | Katie Oreskovich | ||
| 2004 | Best Actress | Mary Ann Laker | Meet My Husbands |
| Best Actor | John Dowers | Meet My Husbands | |
| Best Supporting Actress | Sherri Marrow | The Foreigner | |
| Best Supporting Actor | DJ Sokola | The Foreigner | |
| Cameo | Melody Hull | Meet My Husbands | |
| Jean Lewis Scholarship | Joe Dale Thomas | ||
| 2005 | Best Actress | Gaye Garner | Web of Murder |
| Best Actor | Sonny Downing | Dr. Cook's Garden | |
| Best Supporting Actress | Donna Sant | Barefoot in the Park | |
| Best Supporting Actor | Dave Laker | Barefoot in the Park | |
| Backstage Award | Mike and Leslie Boedicker | In Recognition and Appreciation of Dedication and Loyalty to Red Mask | |
| Jean Lewis Scholarship | Brian Morgan | ||
| 2006 | Best Actress | Jamie DeVore | Angel Street |
| Best Actress | Donna Sant | Desk Set | |
| Best Actor | Randy Offner | Angel Street | |
| Best Supporting Actress | Julia Reynolds | Angel Street | |
| Best Supporting Actor | Nathan Ingold | Come Back to the 5 and Dime, Jimmy Dean, Jimmy Dean | |
| Cameo | Suzie Harmon | Desk Set | |
| Jean Lewis Scholarship | Johnny Howard | ||
| 2007 | Best Actress | Lisa Richter | Bell, Book and Candle |
| Best Actor | John Dowers | Flaming Idiots | |
| Best Supporting Actress | Julia Megan Sullivan | Flaming Idiots | |
| Best Supporting Actor | Sonny Downing | Bell, Book and Candle | |
| Backstage Award | Bev Nees | In Recognition and Appreciation of Dedication and Loyalty to Red Mask | |
| Jean Lewis Scholarship | Ronald Eberhardt, Jr. | ||
| 2008 | Best Actress | Lorraine Morgan | Goodbye Charlie |
| Best Actor | Chuck Pundt | Goodbye Charlie | |
| Best Supporting Actress | Jamie DeVore | Goodbye Charlie | |
| Best Supporting Actor | Ted Sant | Don't Drink the Water | |
| Cameo | Wilbur Bolton | Goodbye Charlie | |
| Jean Lewis Scholarship | Erick Henderson | ||
| 2009 | Best Actress | Nancy Henderson | On Golden Pond |
| Best Actor | Jason Asaad | Over the River and Through the Woods | |
| Best Supporting Actress | Jamie DeVore | Moon Over Buffalo | |
| Best Supporting Actor | Sonny Downing | Over the River and Through the Woods | |
| Backstage Award | Chris Jacobs | In Recognition and Appreciation of Dedication and Loyalty to Red Mask | |
| Jean Lewis Scholarship | Kelsey Daugherty | ||