This article explores the syntactic and semantic relations underlying oxymoronic constructions in Uzbek literary and colloquial discourse. While oxymoron is traditionally treated as a stylistic figure based on semantic contradiction, this study demonstrates that its internal structure is governed by systematic syntactic connections and valency patterns. Drawing upon examples from contemporary Uzbek literature, the article identifies five major types of syntactic relations within oxymoronic expressions: predicative, attributive, objective, circumstantial, and oppositive. Through detailed linguistic analysis, it is shown that despite their paradoxical semantics, oxymorons preserve grammatical coherence and reveal subtle mechanisms of expressivity, emotional intensity, and cultural coding. The findings affirm that oxymoron, as a syntactic phenomenon, not only enhances stylistic effect but also reflects the richness of Uzbek conceptual and communicative frameworks.