Drama Desk Award for Outstanding Featured Actress in a Musical

! style="width:10%;"| Year

! style="width:30%;"| Actress

! style="width:30%;"| Musical

! style="width:30%;"| Character

| Donna Theodore

| Shenandoah

| Ann Anderson

| The Rocky Horror Show

| Columbia

| The Night That Made America Famous

| Various Characters

| The Wiz

| Evillene

| Gypsy

| Baby June

| Shenandoah

| Jenny Anderson

| Vivian Reed

| Bubbling Brown Sugar

| Marsha / Young Irene

| Very Good Eddie

| Madame Matroppo

| The Robber Bridegroom

| Salome

| Dorothy Loudon

| Annie

| Miss Hannigan

| Porgy and Bess

| Serena

| Guys and Dolls

| Sarah Brown

| The Robber Bridegroom

| Salome

| She Loves Me

| Ilona Ritter

| Swoosie Kurtz

| A History of the American Film

| Bette

| Bobo Lewis

| Working

| Rose / Grace / Fran / Lucille

| The Best Little Whorehouse in Texas

| Amber

| Working

| Babe / Terry / Delores

| Merle Louise

| Sweeney Todd

| Lucy Barker / The Beggar Woman

| Ballroom

| Angie

| Eubie!

| Various Characters

| Carmelina

| Rosa

| Platinum

| Crystal Mason

! style="width:10%;"| Year

! style="width:30%;"| Actress

! style="width:30%;"| Musical

! style="width:30%;"| Character

| Debbie Allen

| West Side Story

| Anita

| A Day in Hollywood / A Night in the Ukraine

| Mrs. Pavlenko

| Tintypes

| Performer

| God Bless You, Mr. Rosewater

| Sylvia Rosewater

| The 1940's Radio Hour

| Ginger Brooks

| Tintypes

| Performer

| Marilyn Cooper

| Woman of the Year

| Jan Donovan

| Your Arms Too Short to Box with God

| Performer

| Perfectly Frank

| Performer

| Liliane Montevecchi

| rowspan="2"| Nine

| Liliane La Fleur

| Anita Morris

| Carla Albanese

| Joseph and the Amazing Technicolor Dreamcoat

| The Narrator

| Nine

| Claudia

| The First

| Rachel

| Karla Burns

| Show Boat

| Queenie

| Merlin

| Philomena

| The Cradle Will Rock

| Ella Hammer

| Catherine Cox

| Baby

| Pam Sakarian

| Lila Kedrova

| Zorba

| Madame Hortense

| Doonesbury

| Boopsie

| The Human Comedy

| Kate

| Taking My Turn

| Edna

| Leilani Jones

| Grind

| Satin

| Grind

| Romaine

| The Three Musketeers

| Milady de Winter

| Hang on to the Good Times

| Performer

| Jana Schneider

| The Mystery of Edwin Drood

| Helena Landless / Janet Conover

| Big Deal

| Phoebe

| Singin' in the Rain

| Lina

|Mayor

|Performer

| Sweet Charity

| Nickie

| Jane Summerhays

| Me and My Girl

| Jaqueline 'Jackie' Carstone

| Stardust

| Performer

| Funny Feet

| Various Characters

| Rags

| Bella Cohen

| Cosette

| Rags

| Rachel Halpern

| Joanna Gleason

| Into the Woods

| The Baker's Wife

| Into the Woods

| Little Red Ridinghood

| Flora the Red Menace

| Comrade Charlotte

| The Phantom of the Opera

| Carlotta

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! style="width:10%;"| Year

! style="width:30%;"| Actress

! style="width:30%;"| Musical

! style="width:30%;"| Character

| Randy Graff

| City of Angels

| Oolie / Donna

| Aspects of Love

| Jenny Dillingham

| Grand Hotel

| Freida Flamm / Flaemmchen

| Gypsy

| Louise

| Karen Ziemba

| And the World Goes 'Round

| Various Characters

| The Secret Garden

| Martha Sowerby

| The Secret Garden

| Lily

| A Little Night Music

| Madame Armfeldt

| Tonya Pinkins

| Jelly's Last Jam

| Anita

| The Most Happy Fella

| Cleo

| Crazy for You

| Irene Roth

| Falsettos

| Trina

| Andrea Martin

| My Favorite Year

| Alice Miller

| Putting It Together

| Amy

| Hello Muddah, Hello Faddah!

| Various Characters

| Carnival!

| Rosalie

| Putting It Together

| The Younger Woman

| Audra McDonald

| Carousel

| Carrie Pipperidge

| Hello Again

| The Nurse

| She Loves Me

| Ilona Ritter

| Hello Again

| The Whore

| Annie Warbucks

| Commissioner Harriet Doyle

| Rachel York

| Victor/Victoria

| Norma Cassidy

| Company

| Amy

| Swinging on a Star

| Various Characters

| State Fair

| Emily Arden

| Forbidden Hollywood

| Various Characters

| Lillias White

| The Life

| Sonja

| Chicago

| Matron "Mama" Morton

| Candide

| Old Lady

| Steel Pier

| Shelby Stevens

| I Love You, You're Perfect, Now Change

| Woman #1

| The Green Heart

| Mrs. Tragger

| Tsidii Le Loka

| The Lion King

| Rafiki

| Triumph of Love

| Hesione

| On the Town

| Hildy Esterhazy

| High Society

| Dinah Lord

| The Capeman

| Esmeralda Agrón

| Cabaret

| Fraulein Kost

| Kristin Chenoweth

| You're a Good Man, Charlie Brown

| Sally Brown

| It Ain't Nothin' But the Blues

| Various Characters

| The Civil War

| Bessie Toler

| A New Brain

| Mimi Schwinn

| Fosse

| Various Characters

| It Ain't Nothin' But the Blues

| Various Characters

! style="width:10%;"| Year

! style="width:30%;"| Actress

! style="width:30%;"| Musical

! style="width:30%;"| Character

| Karen Ziemba

| Contact

| Wife

| Jolson and Co.

| Mae West

| James Joyce's The Dead

| Aunt Julia Morkan

| The Wild Party

| Dolores

| rowspan=2| The Wild Party

| Madelaine True

| Kate

| Cady Huffman

| The Producers

| Ulla Swanson

| Follies

| Carlotta Campion

| The Full Monty

| Jeanette Burmeister

| A Class Act

| Sophie

| Urinetown

| Little Sally

| Seussical

| Gertrude McFuzz

| Harriet Harris

| Thoroughly Modern Millie

| Mrs. Meers

| The Spitfire Grill

| Shelby

| Mamma Mia!

| Rosie Mulligan

| Oklahoma!

| Aunt Eller

| Mamma Mia!

| Tanya Chesham-Leigh

| Into the Woods

| The Baker's Wife

| Jane Krakowski

| Nine

| Carla Albanese

| Hairspray

| Penny Pingleton

| Nine

| Luisa Contini

| Urban Cowboy

| Aunt Corene

| Nine

| Lillane La Fleur

| Cookin' at the Cookery

| Young Alberta Hunter

| Isabel Keating

| The Boy from Oz

| Judy Garland

| The Musical of Musicals (The Musical!)

| Various Characters

| Listen to My Heart

| Various Characters

| Caroline, or Change

| Emmie Thibodeaux

| The Thing About Men

| Woman

| First Lady Suite

| Lorena Hickock

| Jan Maxwell

| Chitty Chitty Bang Bang

| Baroness Bomburst

| Dirty Rotten Scoundrels

| Muriel

| Dessa Rose

| Dorcas

| Little Women

| Marmee

| Forbidden Broadway: Special Victims Unit

| Various Characters

| The Light in the Piazza

| Franca Naccarelli

| Beth Leavel

| The Drowsy Chaperone

| Beatrice Stockwell

| Lestat

| Gabrielle

| The Great American Trailer Park Musical

| Pickles

| The Wedding Singer

| Holly

| See What I Wanna See

| Aunt Monica

| Grey Gardens

| Edith Bouvier Beale

| Debra Monk

| Curtains

| Carmen Bernstein

| The Pirate Queen

| Queen Elizabeth I

| Les Misérables

| Éponine

| Legally Blonde

| Paulette

| Company

| Joanne

| Curtains

| Georgia Hendricks

| Laura Benanti

| Gypsy

| Louise

| A Catered Affair

| Jane Hurley

| Young Frankenstein

| Frau Blucher

| Xanadu

| Melpomene / Medusa

| Adding Machine

| Daisy Devore

| 10 Million Miles

| Various Characters

| Haydn Gwynne

| Billy Elliot the Musical

| Mrs. Wilkinson

| The Marvelous Wonderettes

| Missy

| Forbidden Broadway Goes to Rehab

| Various Characters

| West Side Story

| Anita

| The Toxic Avenger

| Mayor

| Pal Joey

| Gladys Bumps

! style="width:10%;"| Year

! style="width:30%;"| Actress

! style="width:30%;"| Musical

! style="width:30%;"| Character

| Katie Finneran

| Promises, Promises

| Marge MacDougall

| The Addams Family

| Alice Beineke

| Lizzie Borden

| Bridget Sullivan

| A Little Night Music

| Madame Armfeldt

| Langston in Harlem

| Zora Neale Hurston

| Finian's Rainbow

| Dottie

| Laura Benanti

| Women on the Verge of a Nervous Breakdown

| Candela

| Catch Me If You Can

| Brenda Strong

| Sister Act

| Mother Superior

| The Kid

| Judith Savage

| The Book of Mormon

| Nabalungi Hatimbi

| Women on the Verge of a Nervous Breakdown

| Lucia

| Anything Goes

| Hope Harcourt

| Judy Kaye

| Nice Work If You Can Get It

| Estonia Dulworth

| Carrie

| Margaret White

| On a Clear Day You Can See Forever

| Melinda Wells

| Follies

| Carlotta Campion

| The Shaggs: Philosophy of the World

| Betty Wiggin

| Bonnie & Clyde

| Blanche Barrow

| Andrea Martin

| Pippin

| Berthe

| Kinky Boots

| Lauren

| Passion

| Clara

| The Mystery of Edwin Drood

| Helena Landless / Miss Janet Conover

| Chaplin: The Musical

| Hannah Chaplin

| Hands on a Hardbody

| Norma Valverde

| The Other Josh Cohen

| Various Characters

| Anika Larsen

| Beautiful: The Carole King Musical

| Cynthia Weil

| Lauren Worsham

| A Gentleman's Guide to Love and Murder

| Phoebe D'Ysquith

| Little Miss Sunshine

| Sheryl Hoover

| After Midnight

| Various Characters

| Fun Home

| Small Alison Bechdel

| The Threepenny Opera

| Polly Peachum

| Disaster!

| Sister Mary Downy

| Renée Elise Goldsberry

| Hamilton

| Angelica Schuyler

| Finding Neverland

| Emma Wightwick du Maurier

| It Shoulda Been You

| Judy Steinberg

| Allegro

| Jenny Brinker

| Pretty Filthy

| Georgina Congress

| Honeymoon in Vegas

| Bea Singer

| On the Town

| Claire De Loone

| Jane Krakowski

| She Loves Me

| Ilona Ritter

| The Color Purple

| Sofia Johnson

| First Daughter Suite

| Betty Ford / Nancy Reagan

| Dear Evan Hansen

| Heidi Hansen

| First Daughter Suite

| Barbara Bush

|Jenn Colella

|Come from Away

|Annette, Beverly Bass, and others

|Hello, Dolly!

|Irene Molloy

|Falsettos

|Trina

|Anastasia

|Dowager Empress Maria Feodorovna

|Spamilton

|Various Characters

|Lindsay Mendez

|Carousel

|Carrie Pipperidge

|Once On This Island

|Mama Euralie

|Mean Girls

|Gretchen Weiners

|My Fair Lady

|Mrs. Higgins

|Mean Girls

|Karen Smith

|Ali Stroker

|Rodgers & Hammerstein's Oklahoma!

|Ado Annie Carnes

|Be More Chill

|Christine Canigula

|Beetlejuice

|Delia Deetz / Miss Argentina

|Carmen Jones

|Frankie

|Tootsie

|Sandy Lester

|Rodgers & Hammerstein's Oklahoma!

|Aunt Eller

! style="width:10%;"| Year

! style="width:30%;"| Actress

! style="width:30%;"| Musical

! style="width:30%;"| Character

| Lauren Patten

| Jagged Little Pill

| Jo

| West Side Story

| Anita

| The Unsinkable Molly Brown

| Ensemble

| The Secret Life of Bees

| August

| Soft Power

| Zoe/Hillary

| Patti LuPone

| Company

| Joanne

| Assassins

| Sara Jane Moore

| Black No More

| Buni

| Kimberly Akimbo

| Debra

| Company

| Sarah