2008–2009 season

Billy Elliot the Musical and Shrek the Musical each received ten nominations, the most of any show. The winners were announced on May 11, 2009, with an awards dinner on May 21 at Sardi's Restaurant.^[1]

Billy Elliot the Musical won seven awards, including Outstanding New Broadway Musical, followed by Shrek the Musical with four. The award for Outstanding Actress in a Musical was a tie between Sutton Foster and Josefina Scaglione. Brian d'Arcy James won for Outstanding Actor in a Musical. Outstanding New Broadway Play was won by God of Carnage.

The John Gassner Award (presented for an American play, preferably by a new playwright) was won by Gina Gionfriddo for Becky Shaw, and the Special Achievement Award was given to the three actors who share the role of Billy Elliot, David Alvarez, Trent Kowalik and Kiril Kulish in Billy Elliot the Musical.^[2]

2009–2010 season

Nominees for the 2009–2010 season were announced on April 26, 2010, by siblings Sutton Foster and Hunter Foster, with winners announced on May 17.^[3] Seven nominations each were received by the musical Memphis and the revival of The Royal Family, the most of any production. The Scottsboro Boys was nominated for six awards, including Best Off-Broadway musical. Shows receiving five nominations were The Addams Family, Bloody Bloody Andrew Jackson, The Orphans' Home Cycle, and Promises, Promises. Finian's Rainbow, La Cage aux Folles, Lend Me A Tenor, and Sondheim on Sondheim each received four nominations.^[4]

The Outstanding New Broadway Musical award was won by Memphis, which won a total of four awards. Other winners included: Outstanding New Broadway Play for Red and Outstanding New Off-Broadway Play for The Orphans' Home Cycle, which won two awards. The Outstanding New Off-Broadway Musical was a tie, won by Bloody Bloody Andrew Jackson and The Scottsboro Boys. La Cage aux Folles won four awards: Outstanding Revival of a Musical, Outstanding Actor In A Musical (Douglas Hodge), Director (Terry Johnson), and Costume Design (Matthew Wright). Montego Glover (Memphis) and Catherine Zeta-Jones (A Little Night Music) tied for Outstanding Actress In A Musical.^[5]

2010–2011 season

The nominees, announced on April 26, 2011, included nine nominations for the musical Sister Act, the most of any show. Anything Goes received eight nominations. The Special Achievement Awards were also announced: Ellen Barkin, Outstanding Broadway Debut in The Normal Heart; and Adrian Kohler with Basil Jones for Handspring Puppet Company Puppet Design, Fabrication and Direction for War Horse.^[6]

The winners were:^[7]

2011–2012 season

The nominees included nine nominations for the new musical Nice Work If You Can Get It, the most of any production, with the musicals Newsies and Once each receiving seven nominations and the revival of Follies receiving five. The Public Theater received an honorary award "on its 50th anniversary presenting free theatre at the Delacorte Theater in Central Park."^[8]

Winners include One Man, Two Guvnors as Outstanding New Broadway Play, Once as Outstanding New Broadway Musical, Sons of the Prophet by Stephen Karam as Outstanding New Off-Broadway Play, and Michael John LaChiusa's Queen of the Mist as Outstanding New Off-Broadway Musical. The Submission by Jeff Talbot received the John Gassner Award.^[9]

2012–2013 season

The nominees included 11 nominations for the revival of the musical Pippin, nine nominations for Kinky Boots, eight nominations (each) for Chaplin: The Musical and Cinderella and six nominations (each) for Golden Boy and The Nance.^[10]

Winners include Vanya and Sonia and Masha and Spike as Outstanding New Broadway Play, Kinky Boots as Outstanding New Broadway Musical, My Name is Asher Lev as Outstanding New Off-Broadway Play and Here Lies Love as Outstanding New Off-Broadway Musical. Who's Afraid of Virginia Woolf? was named Outstanding Revival of a Play and Pippin as Outstanding Revival of a Musical. My Name is Asher Lev by Aaron Posner received the John Gassner Award. The Special Achievement Award was presented to the Irish Repertory Theatre.^[10]

2013–2014 season

The nominees included 11 nominations for A Gentleman's Guide to Love and Murder, 8 nominations for the new musical Aladdin, and 7 nominations for the new musical Fun Home; the dramas Twelfth Night received 5 nominations, Act One 4 nominations, and All the Way 4 nominations.^[11] Winners of multiple awards were A Gentleman's Guide to Love and Murder (including New Musical) with 4; Bullets Over Broadway and The Glass Menagerie with 3 each; and All the Way (including New Play) and Hedwig and the Angry Inch with 2 each. Three plays tied for the John Glassner Award: Eric Dufault, Year of the Rooster; Madeleine George, The (Curious Case of the) Watson Intelligence; and Steven Levenson, The Unavoidable Disappearance of Tom Durnin.^[12]

2014–2015 season

The nominees included Something Rotten! – 12, On the Twentieth Century – 9, An American in Paris – 8, Wolf Hall – 7, It Shoulda Been You – 6, The Audience – 6, The Curious Incident of the Dog in the Night-Time – 6, Hamilton – 5, The Elephant Man – 5, The King and I – 5, The Visit – 5, On The Town – 4, You Can't Take It with You – 4, The Heidi Chronicles – 3 and The Last Ship – 3.^[13]

Multiple winners: The Curious Incident of the Dog in the Night-Time (5, including Outstanding New Broadway Play), An American in Paris (3, including Outstanding New Broadway Musical), Hamilton (3, including Outstanding Off-Broadway Musical), The King and I (3), The Audience (2), On the 20th Century (2) and You Can't Take It With You (2).^[14]

The John Gassner Award winner was The Invisible Hand by Ayad Akhtar.

2015–2016 season

The nominees included American Psycho and She Loves Me – 8; Bright Star and On Your Feet! – 7; Dear Evan Hansen – 6; Eclipsed, Lazarus, Long Day's Journey Into Night and Spring Awakening – 5; and The Humans, A View From the Bridge and Waitress – 4.^[15]

Multiple winners: She Loves Me – 4; Long Day’s Journey Into Night – 3. The Outstanding New Broadway Musical was Bright Star, and the Outstanding New Broadway Play was The Humans; Outstanding Revival of a Play was Long Day’s Journey Into Night and Outstanding Revival of a Musical was She Loves Me. The John Gassner Award winner was Marco Ramirez for The Royale.^[16]

2016–2017 season

The nominees included Anastasia – 13; Hello, Dolly! – 10; The Band's Visit and Come from Away – 7; Groundhog Day – 5; A Bronx Tale – 4; Falsettos, Holiday Inn, and Natasha, Pierre & The Great Comet of 1812 – 3; and Miss Saigon, Sunset Boulevard – 1.^[17]

Multiple winners: Come from Away and Hello, Dolly! – 4; The Band's Visit and Natasha, Pierre & The Great Comet of 1812 – 2. The Outstanding New Broadway Musical was Come from Away, and the Outstanding New Broadway Play was Oslo; Outstanding Revival of a Play was Jitney and Outstanding Revival of a Musical was Hello, Dolly!. The John Gassner Award winner was Bess Wohl for Small Mouth Sounds.^[18]

2017–2018 season

The nominees included SpongeBob SquarePants – 11; Harry Potter and the Cursed Child – 10; My Fair Lady – 9; Mean Girls – 8; Angels in America, Carousel, and Once on This Island – 6; Three Tall Women – 5; Frozen and Prince of Broadway – 4; Farinelli and the King and Travesties – 3.^[19]

The award winners were announced on May 7, 2018. Multiple winners are: Harry Potter and the Cursed Child with six awards, including Outstanding New Broadway Play, and My Fair Lady with five awards, including Outstanding Revival of a Musical. SpongeBob SquarePants won the Outstanding New Broadway Musical, with two additional awards. Jocelyn Bioh, for School Girls; Or, The African Mean Girls Play won the John Gassner Award.^[20]

2018–2019 season

The Outer Critics Circle Award winners for the 2018–19 season include Hadestown (Musical), The Ferryman (Play), Girl From the North Country (Off-Broadway Musical), and White Noise (Off-Broadway Play).

2019-2020 season^[21]