This paper focuses on formation and development of Japanese evaluative adverbial ‘KOTONI’ that can be seen in the Late Middle and Early Modern Japanese, by taking the examples of ‘KOTONI’　similar to the usage of Modern Japanese. As a result, most examples of ‘KOTONI’ up to the Early Middle Japanese were used in the predicate as complements to form noun phrases. When it comes to the Late Middle Japanese, examples of adverbial phrases begin to appear. Since the beginning of the Early Modern Japanese, initial adverbial usage of ‘KOTONI’ was certainly used in the dialogues, not in the descriptive parts. Also through this survey, it is revealed that in the Meiji and Taisho periods, the initial adverbial ‘KOTONI’ was also used, but the initial adverbial ‘MO(e.g. Fushiginimo(不思議にも))’ was still frequently used. Analyzing the examples of the adverbial ‘KOTONI’ from a morphological aspect, there are many examples with ‘WA’ attached to ‘KOTONI’, and the attachment was optional from the Late Middle Japanese to the Modern Japanese. In addition, from the syntactic aspect, it is pointed out that there are constructional change in position of ‘KOTONI’ from the beginning of a sentence to the end of the sentence. In relation to similar cases, examples in which ‘KOTONI’ were adhered to adverbs were confirmed in the Late Middle Japanese as well. Based on present results, it is necessary to comprehensively analyze the initial adverbials including ‘KOTONI’ and ‘MO’.