The purpose of this study is to examine the content of the questions in a number of Advanced Placement Examinations and to attempt to identify content that is related to gender-based performance differences. Free-response questions for ten forms of the AP® Exams in U.S. History, European History, Biology, Microeconomics, and Macroeconomics were studied and the multiple-choice items for four forms of AP U.S. History were also studied. Results indicate that, in the case of U.S. History multiple-choice items, the measures of male and female performance differences are significantly correlated with item content. In a second analysis, the findings for nine of these content categories were replicated in different forms of the exam, suggesting that these results are of generalizable interest. In the case of the free-response questions for each of the five subject areas, the study identified a significant relationship between item content and gender-based performance differences, but there were not enough items for a replication study. Overall, this study suggests that item content is associated with gender-based performance differences. The following are appended: (1) Content Categories for U.S. History Multiple-Choice Items; (2) Content Categories for U.S. History Free-Response Questions; (3) Content Categories for European History Free-Response Questions; (4) Content Categories for Biology Free-Response Questions; (5) Content Categories for Microeconomics Free-Response Questions; and (6) Content Categories for Macroeconomics Free-Response Questions.