In the tv series, 'The Queen's Gambit', eight-year-old Beth Harmon discovers the world of chess and begins her tumultuous journey to become 'queen of the game'. Acute, but not cute, she sets out to navigate her ascent from pawn to White Queen. Veering between madness and intense logicality, Beth’s quest for queenship, against a backdrop of recurrent mirrors, has many similarities with Alice’s experience in 'Through the Looking Glass'. Becoming a queen of the chessboard enriches Beth, whose future looks progressive and reformist; she beats her male competitors, and her addictions, and changes the outlook for female chess masters. Alice’s coronation, however, unsurprisingly for the nineteenth century, suggests regression and degeneration. This paper examines how, despite the fascinating connections between the two stories, Carroll fragments female maturity into atavistic and degenerative figures, thus denying Alice any joy in reaching her queenly destiny; Alice’s queen’s gambit proves a terrible disappointment.