As a word, dengan will always develop as long as it is used by its speakers. The aim of this study is to explain the development of the uses of the word dengan in bahasa Indonesia based on its function as a conjunction or a preposition in a clause from the year 1910 to 2010. The data sources used in this chapter are Indonesian newspapers from the year 1910 to 2010. The methodology used in this chapter is mixed research of quantitative and qualitative approaches. The quantitative approach is used to see the frequency of the uses of dengan. On the other hand, the qualitative approach is used to classify the word dengan into conjunction or preposition; to determine the meaning of the preposition dengan, and to determine the collocation between the verb and the preposition dengan. As a result, (1) dengan as conjunction could function as a subordinate and coordinative conjunction, (2) dengan as a preposition has eleven meanings, (3) the use of the word dengan between 1910 and 2010 as conjunction has been decreasing while the use as a preposition has been increasing, (4) dengan as a preposition could only collocate with certain verbs.