This paper explores Schoenberg's adaptations of dialectical thought within his critical and pedagogical writings. After an introduction that provides a general context for our inquiry, an historical sketch traces significant precursors to Schoenbergian dialectics by outlining key developments in the history of dialectical thought and adaptations of that thought within musical discourse. The paper continues by formulating and discussing various categories of opposition as they are used in music theory in general and in Schoenberg studies in particular. The next three sections of the paper separate Schoenbergian dialectics into three principal areas: Dialectics of History, Dialectical Aspects of Musical Technique, and 'Systems' as Failed Dialectics. Each of these sections centers on close readings of passages from Schoenberg's critical and pedagogical writings. The paper concludes by briefly discussing the implications of dialectical thought for further analysis.