Main topic of this paper is the stylistic structure of the orations of Grigor Prlichev, which were written and performed by the occasion of different religious holidays or dedicated for the end of the study year at different schools where he was teaching throughout Macedonia. Several specifics are to be taken in consideration: elements of cohesion, different ways of addressing, some syntactic characteristics, use of style figures etc. The intonation used by the author should also be taken in regard, although it cannot be subject to analysis for obvious reasons. One of the most important specifics is the use of lithurgical elements, comparisons with biblical motives, use of rhetorical questions, ways of addressing the public with intention of establishing familiarity etc. There is also frequent use of developed poetic images, dialogues with a purpose of developing the topic and promotion of the didactic function. This analysis is a contribution to the further study of the composition of the orations of Grigor Prlichev.