Four-letter-word is a unique phenomenon manifesting the art of Chinese language. Its translation requires the exact conveyance of meaning, the natural reconciliation to context, and the pragmatic consideration reflecting literary grace, all of which involve a lot of challenges. This article is to investigate the translation strategies of four-letter-words from Chinese to Japanese on the basis of the translation practice for the purpose of finding out the solution to possible problems. It starts from the statistical analysis of students' translation work and the problems involved. Then it discusses the functions of the four-letter-words in Chinese and the differences of lexical usage between Chinese and Japanese. Finally, it clarifies the strategies to translate free four-letter-words from the perspectives of synonyms and ambivalent words, with specific steps involved.