Deep cutaneous fungal infections (DCFI) are cutaneous and subcutaneous infectious diseases caused by fungi. Multiple genera of pathogenic fungi have been reported to cause DCFI. Herein, we report three rare cases of Pleosporales deep cutaneous infection in a southern Taiwan medical center. We evaluated the clinical manifestations, histopathological findings, pathogens, treatments and outcomes. The patients were a 77‐year‐old woman, a 78‐year‐old woman and an 81‐year‐old man, who lived in rural tropical areas. The lesions were erythematous noduloplaques with dark spots located on the upper extremities. Sequence‐based identification showed three different fungi of the order Pleosporales, namely Nigrograna mackinnonii, Medicopsis romeroi and Parathyridaria percutanea. All three cases received 200 mg of oral itraconazole daily for 10, 2 and 8 months, respectively. Two of them are free of diseases to date, and one improved partially but did not complete the treatment. Molecular tools are helpful for the identification of DCFI to exact species, which is key to successful treatment.