Serena Williams splayed on a throne for Sports Illustrated, Ashley Harkleroad bending over on Playboy, and Anna Kournikova gazing sultrily on Penthouse, Maxim, and FHM—these are just a few examples of women tennis players showing copious amounts of glistening skin on newsstands since the early 2000s. Since the emergence of the Virginia Slims Tour and its provocative slogan, “You’ve come a long way, baby,” in 1970, it has been clear that sex and women’s tennis are a tight match. But the shared cultural history of sex and tennis precedes the 1970s and the Sexual Revolution. Focused on the period of 1874 to 1960, this article, a prehistory, follows the progression of the intimate and sexy imagery of women tennis players by examining everyday objects and occurrences—parties, paintings, postcards, photography, news and lifestyle magazine covers, pin-up art, film art, victory celebrations, exhibition tours, and panties—to reveal the sometimes shocking yet common and open ways in which women’s participation in tennis was sexualized. Women tennis players carried out their careers in a culture whose paradoxical exaltation and sexualization of their sport brought visibility and opportunities unheard of for women in less expensive and contact sports. Whether embracing, accepting, or recoiling at the situation, all navigated sexualized events, innuendos, and expectations. Part of “the golden age of American sports,” World War II, Wimbledon, and the battle over civil rights, this history casts light and shadow on tennis’s reputation and status as a space of sophistication and liberation for women.