Anna Tschipowskaja ist die Tochter von Olga Tschipowskaja, einer Theaterschauspielerin, und Boris Frumkin, einem Jazzmusiker.

Sie debütierte Anfang der 2000er Jahre als Filmschauspielerin. Nach Nebenrollen in verschiedenen Spielfilmen übernahm sie ab 2005 die Rolle der Sveta Popova in insgesamt 29 Episoden der Fernsehserie Dorogaya Masha Berezina. In den Filmen Yolki 2 von 2011 und dessen Fortsetzung 2013, Yolki 3, übernahm sie die Rolle der Lena. Hauptrollen stellte sie unter anderem in Titanium – Strafplanet XT-59 von 2014, in O – Sexuelles Verlangen von 2017 und Has Anyone Seen My Girl? von 2020 dar.

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