2012

• Creg Sclavi -Actor in a Principal Role — "Urinetown"
• Chuck Sisson -Actor in a Principal Role — "The Baker's Wife"
• Jeremy Rill -Supporting Actor — "A Little Night Music"
• Anita Hoffman- Supporting Actress — "The Baker's Wife"
• Khaki Pixley- Supporting Actress — "A Little Night Music"
• Kevin Bellie - Choreography — "Urinetown"
• Bob Knuth -Scenic Design — "The Women"
• Jesus Perez - Costume Design — "Urinetown"
• Elizabeth Wislar - Costume Design — "A Little Night Music"
• Elizabeth Wislar - Costume Design — "The Women

2011

• ** 2010 Special Award - Circle Theatre - Honoring its contributions to Chicago theatre on Circle Theatre’s 25th anniversary
• Anita Hoffman - Actress in a Supporting Role - Musical - "The Best Little Whorehouse in Texas"
• Noah Sullivan - Actor in a Supporting Role - Musical - "The Best Little Whorehouse in Texas"
• Kevin Bellie - Choregraphy - "The Best Little Whorehouse in Texas"
• Bob Knuth - Scenic Design - "The Philadelphia Story"

2010

• Circle Theatre, Production - Musical, The Who's Tommy
• Jeffrey Cass, Director - Musical, The Who's Tommy
• Tom McGunn, Actor in a Principal Role - Musical, The Who's Tommy
• Eric Lindahl, Actor in a Supporting Role - Musical, The Who's Tommy
• Mary Redmon, Actress in a Supporting Role - Play, The Analytical Engine
• Kevin Bellie, Choreography, The Who's Tommy
• Bob Knuth, Scenic Design, The Analytical Engine
• Bob Knuth, Scenic Design, Little Women
• Elizabeth Powell, Wislar Costuume Design, The Analytical Engine
• Kevin Bellie, Projection Design, The Who's Tommy

2009

• Outstanding Production-Play, Enchanted April
• ** Bob Knuth, Scenic Design, Enchanted April
• ** Mary Redmon, Supporting Actress, Enchanted April
• Suzanne Mann Costume Design, Enchanted April
• ** Suzanne Mann, Costume Design, Hay Fever
• Bob Knuth, Scenic Design, Hay Fever
• Rachel Quinn, Gentlemen Prefer Blondes
• Kevin Bellie, Choreography Gentlemen Prefer Blondes
• Jesus Perez, Costume Design Gentlemen Prefer Blondes

2008

• Circle Theatre Production - Play, An Ideal Husband
• Jim Schneider Director - Play, An Ideal Husband
• ** Elizabeth Shaffer, Costume Design, An Ideal Husband
• Bob Knuth, Scenic Design, An Ideal Husband
• Saren Nofs-Snyder, Actress in a Supporting Role - Play, An Ideal Husband
• Bradford R. Lund, Actor in a Supporting Role - Play, An Ideal Husband
• Circle Theatre, Production-Musical, Seven Brides for Seven Brothers
• Rachel Quinn, Actress in a Principal Role - Musical, Seven Brides for Seven Brothers
• Kevin Bellie, Choreography, Seven Brides for Seven Brothers
• Jeremy Rill Actor in a Principal Role - Musical, Can Can
• ** Elizabeth Lanza, Actress in a Principal Role - Musical, Can Can
• Jesus Perez Costume Design, Can Can

2007

• ** Cat Davis, Actress in a Principal Role - Musical or Revue, Mack and Mabel
• ** Jesus Perez, Costume Design, Mack and Mabel
• Kevin Bellie, Choreography, Mack and Mabel
• Kevin Bellie, Choreography, Meet Me in St. Louis
• Suzanne Mann, Costume Design, Meet Me in St. Louis
• Bob Knuth, Scenic Design, Meet Me in St. Louis
• Bob Knuth, Scenic Design, Stone Cold Dead Serious
• Michael Mahler, Actor in a Principal Role - Musical or Revue, Sweet Smell of Success

2006

• Circle Theatre, Production - Play, What's Wrong With Angry?
• Michael Matthews, Director - Play, What's Wrong With Angry?
• ** Jürgen Hooper, Actor in a Principal Role - Play, What's Wrong With Angry?
• Kelly Schumann, Actress in a Supporting Role-Play, What's Wrong With Angry?
• Tim Rock, Actor in a Supporting Role - Play, What's Wrong With Angry?
• Simone Roos, Actress in a Principal Role - Play, Design for Living
• Robert A. Knuth, Scenic Design, Design for Living

2005

• ** Sarah Swanson, Actress in a Principal Role - Musical or Revue, Jane Eyre
• Marc Pera, Actor in a Principal Role - Musical or Revue, Jane Eyre
• ** Darrelyn Marx, Actress in a Supporting Role - Musical or Revue, Jane Eyre
• Circle Theatre, Production - Musical, The Mystery of Edwin Drood
• Kevin Bellie, Director, The Mystery of Edwin Drood
• ** Jon Steinhagen, Actor in a Pricipal Role - Musical, The Mystery of Edwin Drood
• Megan Van de Hey, Actress in a Supporting Role - Musical, The Mystery of Edwin Drood
• Anita Hoffman, Actress in a Supporting Role - Musical, The Mystery of Edwin Drood
• Walter Tambor, Musical Direction, The Mystery of Edwin Drood
• Kevin Bellie, Choreography, The Mystery of Edwin Drood
• Joel Sutliffe, Actor in a Supporting Role - Musical, The Mystery of Edwin Drood
• Jeffrey Kelly, Costume Design, The Mystery of Edwin Drood
• Audrey Francis, Actress in a Principal Role - Play, The Credeaux Canvas
• Jason Powers, Actor in a Pricipal Role - Play, Credeaux Canvas

2004

• ** Kelly Schumann, Actress in a Supporting Role - Play, Steel Magnolias
• ** Bob Knuth, Scenic Design, Steel Magnolias
• Circle Theatre, Ensemble, Steel Magnolias
• Circle Theatre, Production - Play, In The Blood
• Circle Theatre, Ensemble, In The Blood
• Michael Matthews, Director - Play, In The Blood
• Inda Craig-Galvan, Actress in a Principal Role - Play, In The Blood
• Kurt Ottinger, Lighting Design, Fool For Love
• Peter J. Storms, Sound Design, Fool For Love

2003

• ** Circle Theatre, Production – Musical, The Secret Garden
• ** Sarah Swanson, Actress In A Supporting Role - Musical, The Secret Garden
• ** Kevin Bellie, Choreography, The Secret Garden
• ** Jeffrey Kelly, Costume Design, The Secret Garden
• Bob Knuth, Director – Musical, The Secret Garden
• Bob Knuth, Scenic Design, The Secret Garden
• Mark Pera, Actor In A Principal Role - Musical, The Secret Garden
• Brooke Sherrod, Actress In A Supporting Role - Musical, The Secret Garden
• Jacob Hoffman, Actor In A Supporting Role - Musical, The Secret Garden
• Jon Steinhagen, Musical Direction, The Secret Garden
• ** Stephen Clark, New Work, Stripped
• Meghan M. McDonough, Actress In A Principal Role - Play, Stripped
• Lynn Ann Bernatowicz, Director – Play, Stripped
• Jason Bradley, Actor In A Principal Role - Play, Stripped
• Richard Schneider, Scenic Design, Stripped

2002

• Circle Theatre, Ensemble, Nine: the Musical
• Kevin Bellie, Direction, Nine: the Musical
• Carl Haan, Musical Direction, Nine: the Musical
• ** Jeffrey Kelly, Costume Design, Nine: the Musical
• Katie Johnston, Supporting Actress, Moon's the Madonna

2001

• ** Kevin Bellie, Choreography, Triumph Of Love
• ** Jeffrey Kelly, Costume Design, Triumph Of Love
• John Simmons, Supporting Actor, Triumph Of Love
• Jon Steinhagen, Musical Direction, Triumph Of Love
• Bob Knuth, Scenic Design, Triumph Of Love
• Kevin Bellie, Choreography, The Life
• Bob Knuth, Scenic Design, The Life
• Rick Young, Scenic Design, American Buffalo

2000

• ** Circle Theatre, Production, The Crime Of The Century
• ** Greg Kolack, Direction, The Crime Of The Century
• ** Seema Sueko, Principal Actress, The Crime Of The Century
• ** Rebecca Gilman, New Adaptation, The Crime Of The Century
• ** Jennifer Fisk, Supporting Actress, The Cover Of Life
• ** Bethanny Alexander, Principal Actress, The Cover Of Life
• Ty Perry, Choreography, Eating Raoul

1999

• Circle Theatre, Production, Lips Together, Teeth Apart
• ** David Krajecki, Patrick Uphues, Scenic Design Lips Together, Teeth Apart
• Bethanny Alexander, Principal Actress, Murder In Green Meadows
• Janelle Snow, Supporting Actress, Auschwitz Lullaby

1998

• ** Circle Theatre, Production, Who's Afraid Of Virginia Woolf?
• ** Alena Murguia, Direction, Who's Afraid Of Virginia Woolf?
• Patti Paul, Principal Actress, Who's Afraid Of Virginia Woolf?
• Greg Kolack, Principal Actor, Who's Afraid Of Virginia Woolf?
• Bethanny Alexander, Supporting Actress, Who's Afraid Of Virginia Woolf?
• Karen Skinner, Scenic Design, Who's Afraid Of Virginia Woolf?
• Kevin Bellie, Direction, Grand Hotel
• Kevin Bellie, Almir Hodzic, Quiana Markham, Keith Schneider, Costume Design, Grand Hotel
• ** John Simmons, Supporting Actor, Grand Hotel
• ** Kevin Bellie, Choreography, Grand Hotel
• ** Jon Steinhagen, Musical Direction, Grand Hotel
• Doug MacKechnie, Principal Actor, Principia Scriptoria

1997

• ** Deborah Puette, Principal Actress, The Glory Of Living
• ** Robin Stanton, Direction, The Glory Of Living
• ** Marty Higgenbotham, Principal Actor, The Glory Of Living
• ** Rebecca Gilman, New Work, The Glory Of Living
• ** Janelle Snow, Supporting Actress, Five Women Wearing The Same Dress
• Greg Kolack, Direction, Five Women Wearing The Same Dress
• Circle Theatre, Ensemble, Five Women Wearing The Same Dress
• Jeffrey Kolack, Scenic Design, Five Women Wearing The Same Dress

1995

• ** Jon Steinhagen, Original Incidental Music, A Piece Of My Heart
• ** Circle Theatre, Production, A Piece Of My Heart
• ** Circle Theatre, Ensemble, A Piece Of My Heart
• ** Greg Kolack, Direction, A Piece Of My Heart