This work explores the characteristics and establishes the historical significance of James Scarth Gale(1863-1937)’s unpublished English translations of Korean classical Sijo(時調). In the Thomas Fisher Rare Book Library belonging to the University of Toronto, Canada lies unpublished translations of Korean classics; part of this collection is a typed unpublished book called Pen-Pictures of Old Korea(『朝鮮筆景』) and a manuscript called The Diary(『日誌』) which contains English translations of Korean classical Sijo. During Gale’s 40 year stay in Korea, he devoted 30 of those years to translating Sijo. Previous research shows Gale’s translations differ in demeanor and purpose by publication period. Specifically, the first series of translations, those published in The Korean Repository between 1895 to 1898, was translated with the English audience in mind. On the other hand, the second series of translations, those published in The Korea Bookman in 1922, strives to highlight the literary qualities of the source. The last series of translations, published between 1924 and 1927 in The Korean Mission Field, amalgamate qualities of the previous two in attempt to please a broader audience. The Pen-Pictures of Old Korea, which was set to be published in 1912 but remains unpublished, shows similar qualities to that of Gale’s first series of translations. Although the first series of translations encompasses a large and diverse array of media, judging by time and its attributes, The Pen-Pictures of Old Korea can effectively be categorized into his first series of translations. Assuming such, we arrive at the notion that Gale translated as a service to Western literature until the early 1910s. Regarding The Diary(『日誌』), previous research has unveiled its publication period as similar to that of The Korea Bookman, the second series of translations. The two works are similar in its originalist motivations, but there also exist points of distinctions. Considering these qualities, we can assume that The Korea Bookman was written prior to The Diary, and The Diary was written to supplement and expand the subject The Korea Bookman was based off of. Through the discovery of The Diary, as Gale emphasized in The Korea Bookman, we arrive at the conclusion that Gale paid respects to the Korean traditional culture and continuously attempted to publicize such to the Western society.