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Empirically, in Indonesia, the leaves of <i>Cassia alata</i> L. (candle bush or ketepeng cina) have been used as a topical antifungal agent. <i>Malassezia furfur</i> is a natural microorganism found in the human body. It is among the factors contributing to conditions such as pityriasis versicolor, a common, benign, superficial fungal infection of the skin that is closely associated with seborrheic dermatitis and dandruff. This study aimed to explore <i>C. alata</i> leaves, starting from determining antifungal activity against <i>M. furfur</i> and the identification of major compounds in the ethyl acetate and n-hexane fractions, and then we carried out molecular docking of the major compounds in the n-hexane fraction to lanosterol 14-alpha demethylase. The method was the disc diffusion technique to test antifungal activity, LC-MS/MS for major compound identification, and homology modeling through Swiss Models for molecular docking. The fractions of ethyl acetate and n-hexane extract showed concentration-dependent antifungal activity against <i>M. furfur</i>. The LCMS/MS analysis revealed five major compounds in the ethyl acetate and n-hexane fractions. The molecular docking demonstrated the highest binding affinity with stearidonic acid at −7.2 kcal/mol. It can be concluded that the compounds in the n-hexane fraction have antifungal activity against <i>M. furfur</i>, as supported by both in vitro and in silico studies.