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How do women become leaders of major political parties? In parliamentary systems, the party leader position is the penultimate step to becoming prime minister, and hence is the threshold to the most powerful position in parliamentary governments. This paper uses the universe of Conservative and Labour Party leadership contests in the United Kingdom for the years 1975-2020 to test three explanations for women’s success in becoming party leader: ambition, strategic candidacy, and glass cliffs. The first two explanations derive from studies of parliaments and legislative candidacies; the third derives from studies of managerial promotion opportunities in business. The paper presents each of these potential explanations and tests them for candidates, potential candidates, and eventual winners in party leadership contests. The paper draws conclusions about the specific nature of and high elite level of political leader contests and the extent to which the results for the UK major parties are gendered and generalizable.