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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.

• Drama Desk Award for Outstanding Director of a Play
• Drama Desk Award for Outstanding Director of a Musical