Vocabulary can have multiple meanings. In general, the meanings of polyseme- a word that has several meanings- are closely related to each other. In a particular case, however, a polysemous word or phrase has completely opposite meanings. As a follow-up study of Choi (2015), the current study aims to classify and analyze polysemous words and phrases that include contradictory meanings with a focus on their distinctiveness. Based on the cause of contradictoriness, polysemous words and phrases with conflicting definitions were classified into five different categories which are ‘contradictory homonyms’, ‘morphologic polysemes with contradictory definitions’, ‘semantic polysemes with contradictory definitions’, ‘syntactic phrases with contradictory definitions’, and‘syntactic and semantic phrases with contradictory definitions.’ Furthermore, several examples are discussed in this study to enhance understanding. For instance, the examples of contradictory homonyms include‘심심하다[simsimhada]’, ‘일절[iljeol]’ and some Chinese characters that have same sound but opposite meanings. The examples of morphologic polysemes with contradictory definitions are ‘등[deung]’,‘값없다[gabeoptta]’,‘세내다[senaeda]’, ‘N조심 [N+josim]’, ‘웃프다[upeuda]’and ‘착쁘다[chakppeuda].’Also, the examples of semantic polysemes with contradictory definitions are ‘안절부절하다 [anjeolbujeolhada]’, ‘우연찮다[uyeonchanta]’, ‘어줍잖다[eojupjanta]’, and ‘꼴같다[kkolgatta].’ With a list of classified words and phrases, the researcher conducted a survey and integrated Korean linguistic analysis to explain polysemous words or phrases with contradictory definitions and finally chose a representative definition between two conflicting ones.