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  1. 9 ore fa · The Best Supporting Actress award has been presented a total of 88 times, to 86 actresses. The first winner was Gale Sondergaard for her role in Anthony Adverse. The most recent winner is Da'Vine Joy Randolph for her role in The Holdovers. [3] The record for most wins is two, held jointly by Dianne Wiest and Shelley Winters.