“Gypsy Robe” Winners
The “Gypsy Robe” award is given to the outstanding member of the ensemble.
| Name | Show | Date |
| Frankie Jensen | James and the Giant Peach | January 2018 |
| Allison Udelhoven & Sophia Wagganer | Footloose | July 2017 |
| Sydney Bush | Joseph and the Amazing Technicolor Dreamcoat |
January 2017 |
| Gabrielle Simpson | Beauty and the Beast | July 2016 |
| Samantha Chen & Bryce Harrison | The Little Mermaid | January 2016 |
| Jasmine Lew | Mary Poppins | July 2015 |
| Rachel Ho & Gisele Lajevardi | Seussical | January 2015 |
| Molly O’Donnell | Shrek | August 2014 |
| Karl Lola | Peter Pan | January 2014 |
| Lucas Williams | All Shook Up | August 2013 |
| Katherine Hall | A Little Princess | January 2013 |
| Cheyenne Wells | Legally Blonde | July 2012 |
| Jennica Christman | The Adventures of Tom Sawyer | January 2012 |
| Devon Simpson | Guys and Dolls | July 2011 |
| Samantha Rasler | Annie | January 2011 |
| Lauren D’Ambrosio | Les Misérables | July 2010 |
| Gelsey Plaza | The Music Man | January 2010 |
| Trevor Meyer | CATS | July 2009 |
| Leyna Conover | Wizard of Oz | January 2009 |
| James M. Jones | 42nd Street | August 2008 |
| Annalisa Panelli | 42nd Street | August 2008 |
| Charles Platt | Honk! | January 2008 |
| Kyle Burgess | Beauty & the Beast | August 2007 |
| Amy Mendonca | Peter Pan | January 2007 |
| Brian Estrada | Thoroughly Modern Millie | July 2006 |
| Jeremy Bontadelli | Aladdin Jr. | April 2006 |
| Beatrice Crosbie | Frog and Toad | January 2006 |
| Lauren Hillman | Anything Goes | August 2005 |
| Alison Lenci | Seussical | January 2005 |
| Matthew Sa | Bye Bye Birdie | August 2004 |
| Laura Hendrickson | Oliver | May 2004 |
| Michelle Foletta | Oliver | May 2004 |
| Jessica Christman | Honk | December 2003 |
| Juliane Godfrey | Into the Woods | July 2003 |
| Sarah Thomsen | School House Rock Live | April 2003 |
| Rachel Nuno | Hansel and Gretel | November 2002 |
| “The Apprentices” | Babes in Arms | July 2002 |
| Ben Nguyen | Annie | April 2002 |
“Director’s Award” Winners
The Director’s Award is given each year to an outstanding actor or actress.
- 2011 – Trevor Meyer, Chelsey Sue, Karina Simpson, Grace Goreniger
- 2010 – Connor Stokes, Benjamin Hall, Kimberly Chatterjee, Michael Jon Landreth, James Jones, Daniel J. Harper, Jeremy Bontadelli, Kyle Jones, Scott Kavanagh, Trevor Meyer
- 2009 – Benjamin Hall, Rebecca Crosbie, Drew Williams
- 2008 – Esteban Gonzalez, Jessica Christman, Beatrice Crosbie, Drew Williams, Jordan Aragon Devon Simpson
- 2007 – Michelle Foletta, Julian Godfrey, Ray Mendonca, James Jones, Natalie Hawkins, Evan Boomer, Lance Smith
- 2006 – Evan Boomer, Jordan Aragon, Esteban Gonzalez, Lauren Hall, Melissa Modifer, Courtney Stokes
- 2005 – Juliane Godfrey, Anthony Vega, Laura Sa, Courtney Stokes, Antonio Mungia
- 2004 – Stacey Lynn Bell, Emily Matthews
- 2003 – Courtney Stokes, James Huang
- 2002 – Andrew Sa
- 2001 – Max Wirt, Nicole Randolph
- 2000 – Jessica Weiss
- 1999 – Megan Gallup, Kristin Stokes
