Drama Desk Award for Outstanding Director

This is a list of winners of the Drama Desk Award for Outstanding Director introduced in 1955 to honour directors, with no distinction between work in plays or musicals. From 1968, multiple awards were presented for each season. In 1975 the category was retired and replaced by two awards: Drama Desk Award for Outstanding Director of a Play and Drama Desk Award for Outstanding Director of a Musical.

1950s

 * 1955: Jack Landau – The Clandestine Marriage / The White Devil
 * No nominees
 * 1956: José Quintero – The Iceman Cometh
 * No nominees


 * 1959: William Ball – Ivanov
 * No nominees

1960s

 * 1965: Ulu Grosbard – A View from the Bridge
 * No nominees
 * 1967: Joseph Hardy – You're a Good Man, Charlie Brown
 * No nominees
 * 1968: Robert Moore – The Boys in the Band and Tom O'Horgan – Tom Paine
 * No nominees


 * 1969: Tom O'Horgan – Futz
 * Neal Kenyon – Dames at Sea
 * Alan Arkin – Little Murders
 * Michael Schultz – Does a Tiger Wear a Necktie?
 * Gordon Davidson – In the Matter of J. Robert Oppenheimer
 * Edwin Sherin – The Great White Hope
 * No nominees

1970s

 * 1970: Jerzy Grotowski – The Apocalypse
 * Alan Arkin – The White House Murder Case
 * Ron Field – Applause
 * Joseph Hardy – Child's Play
 * Harold Prince – Company
 * No nominees
 * 1971: Robert Wilson – Deafman Glance
 * Andre Gregory – Alice in Wonderland
 * Peter Brook – A Midsummer Night's Dream
 * Michael Bennett – Follies
 * Harold Prince – Follies
 * Tom O'Horgan – Lenny
 * Paul Sills – Ovid's Metamorphoses and Paul Sills' Story Theatre
 * No nominees
 * 1972: Mel Shapiro – Older People
 * Andrei Șerban – Medea
 * Peter Hall – Old Times
 * Jeff Bleckner – Sticks and Bones
 * A. J. Antoon – That Championship Season
 * Mel Shapiro – Two Gentlemen of Verona
 * No nominees


 * 1973: Victor Garcia – Yerma
 * Joseph Chaikin – The Mutation Show
 * Roberta Sklar – The Mutation Show
 * Harold Prince – A Little Night Music
 * Bob Fosse – Pippin
 * Michael Rudman – The Changing Room
 * Harold Prince – The Great God Brown
 * No nominees
 * 1974: José Quintero – A Moon for the Misbegotten
 * Harold Prince – Candide
 * Frank Dunlop – Scapino
 * Marvin Felix Camillo – Short Eyes
 * Harold Prince – The Visit
 * No nominees