Beginning and ending a work in the same key, thereby suggesting a hierarchical structure, is a hallmark of eighteenth- and nineteenth-century practice. Occasionally, however, early nineteenth-century works begin and end in different, but equally plausible keys (directional tonality), thereby associating two or more keys in decentralized complexes. Franz Schubert’s works are sometimes interpreted as central to this practice, especially those that extend third relationships to larger, often chromatic cycles. Robert Schumann’s early directional-tonal works, however, have received less analytical scrutiny. In them, pairings are instead diatonic between two keys, which usually relate as relative major and minor, thereby allowing Schumann to both oppose and link dichotomous emotional states. These diatonic pairings tend to be vulnerable to monotonal influences, with the play between dual-tonal (equally structural) and monotonal contexts central to the compositional discourse. In this article, I adapt Schenkerian theory (especially the modifications of Deborah Stein and Harald Krebs) to directional-tonal structures, enumerate different blendings of monotonal and directional-tonal states, and demonstrate structural play in both single- and multiple-movement contexts.