Candidiasis, an opportunistic infectious condition caused by the genus Candida, is the most common oral fungal infection in humans. The diagnosis of oral candidiasis can often be made based on recognition of its clinical pattern, but at times there is difficulty in making a clinical diagnosis because of its various manifestations. Several antifungal medications have been developed for managing fungal infections. Despite the availability of several effective antimycotics for the treatment of oral candidiasis, failure of therapy is not uncommon due to the unique environment of the oral cavity, where the flushing effect of saliva and the cleaning action of the oral musculature tend to reduce the drug concentration to sub-therapeutic levels. In this case report, we present two patients diagnosed with chronic hyperplastic candidiasis and median rhomboid glossitis, which are known as rare forms of candidiasis. In both cases, there was a significant reduction of clinical signs and symptoms when fluconazole was prescribed after the failure of initial nystatin therapy.