In the 15th and early 16th centuries, educational life at the universities of Western and Central Europe was dominated by serious doctrinal conflicts between several schools of thought (the Antiqui/Reales vs the Moderni/Nominales), the Wegestreit. This clash not only had serious consequences for instruction in philosophy and theology, but was also felt in the grammar courses of the BA programme. Remarkably, we find the old elementary grammar primer, the Donatus minor, as a prescribed textbook in several Arts faculties. This essay examines the impact of the so-called Wegestreit on university grammar instruction with special reference to late 15th- and early 16th-cent. commentaries on the Donatus minor. After a concise sketch of the philosophical and logical roots of the Wegestreit, I present the development of the conflicting approaches to language and grammar in the 14th century that underlay the divergent opinions of the 15th-century masters. The third section deals with the position of the Donatus minor as a textbook for the undergraduate grammar courses of the Arts faculties. The remainder of this essay falls into two sections. First, a discussion of the different ways the Antiqui and Moderni analyse and explain some theoretical and the related practical aspects of syntactic relations in the last decades of the 15th cent. This part is followed by two case studies of the analyses, explanations and applications of these syntactic phenomena in the commentaries on the Donatus minor of the Realist/Thomist, Magnus Hundt (1449-1519) of Leipzig, and the Modernist Florentius Diel (fl. 1490-1509) of Mainz.