Liberal political changes in the Habsburg monarchy during the 1860s and 1870s, especially those caused by the December Constitution of 1867 and the ensuing schooling laws, created the necessary legal framework for German and Czech school associations to establish national monolingual schools in Bohemia—the so-called minority schools. These local organizations, however, were soon superseded by central school associations, namely the German association in Vienna (Deutscher Schulverein) and the Czech one in Prague (Ústřední Matice Školská). Founded in 1880, these associations were aimed at schools in the linguistically, and therefore nationally, contested regions along the “language frontier.” This study focuses on the dynamics of the national contestation over schooling prior to World War I and compares the activities of these two associations against the background of political democratization, mass mobilization, and the social questions of the fin de siècle. The comparative analysis of the proclamations, activities, and political contacts of the competing central school associations aims at revising theses about the position and meaning of these organizations and shows their very close interdependence upon political processes, especially on the unsuccessful Czech-German negotiations on a national compromise for Bohemia.