This work examines the development of the two main chess allegories in German literature from the twelfth to the fourteenth century focusing on the issue of gender. Chess was a common allegory for political negotiation on the one hand, and courtly love on the other. In the political chess allegory, women are typically absent. In the courtly love chess allegory, women have a central role but it is usually a passive one. I will show that these two allegories did not develop separately, but intersected at some points, granting power to the female sex. A space for female agency is created when poets draw on both allegories, and chess can actually lead the ladies away from their passive role in the love allegory by means of the political allegory. This will be demonstrated in scenes from Wolfram's Parzival and Gottfried's Tristan, and in one illumination found in the Manesse Codex.