This thesis offers insightful suggestions regarding the interdisciplinary approach of utilizing Korean language history in high school classic literature in Korean language education. The Middle Korean interrogative system and the pre-final ending “-오-” were selected as core grammatical elements and applied to Kyuwonga and Jeongseokga. The findings confirmed that linguistic knowledge significant for appreciation is directly linked to understanding the speaker’s socio-cultural context and the content of the work. Thus, a hierarchy of knowledge can be established, ranging from foundational elements (orthography, phonology, and basic vocabulary) to advanced elements that facilitate a nuanced understanding of expressive intents. Accordingly, a specific instructional design was proposed comprising three stages: ‘Modern Korean Translation (Foundation) → Capturing Grammatical Clues (In-depth) → Deep Emotional Reception (Expansion).’ This study is significant in that it facilitates the integrated improvement of both literary and linguistic abilities by transforming grammatical knowledge into a practical linguistic resource for generating and interpreting meaning.