- Winwood's best friend from the 1920s until her death in the 1960s was Tallulah Bankhead.
- At the time of her death (at age 101) she was the all-time oldest member of the Screen Actor's Guild.
- George Cukor died only hours after sending her a telegram for her 100th birthday.
- When she was 95, she acknowledged on Merv Griffin's talk show that she smoked three packs of cigarettes a day.
- Her first husband, Arthur Chesney, was the brother of Edmund Gwenn.
- Holds the distinction of playing the last client to be defended by Perry Mason in the 1957-66 TV series by that name.
- When she took on her final major television role in a 1979 episode of Quincy, she officially became, at age 96, the oldest actor working in the U.S., narrowly beating fellow British actress Ethel Griffies.
- On her 100th birthday, Winwood was asked how it felt to have lived so long, she replied "How rude of you to remind me!".
- With her mother's support, but her father's disapproval, she trained with the Lyric Stage Academy in London, before making her professional debut in Johannesburg at the age of 20.
- She is sometimes confused with the classic Hollywood comic scream queen Una O'Connor.
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