Eumycetoma is a chronic, progressive infection characterized by granulomatous inflammation, commonly affecting the skin, subcutaneous tissues, and bones. This case study presents the complex management of a 27-year-old male patient with a recurrent eumycetoma caused by Madurella mycetomatis in both feet. Initially diagnosed in 2019, the patient underwent multiple surgical excisions and antifungal treatments over the years, including itraconazole, terbinafine, and posaconazole. The patient’s condition remained refractory, with recurrent nodules and ulcerations developing on both feet, despite intensive medical and surgical management. In 2024, the patient was admitted to the Bernhard Nocht Institute of Tropical Medicine in Hamburg for further treatment. MRI imaging revealed a persistent granulomatous lesion in the right foot with involvement of the m. adductor hallucis. Despite treatment with posaconazole, the patient experienced significant clinical deterioration, including the development of a new eumycetoma lesion on the left foot. Surgical excisions were performed on both feet, and histopathology confirmed eumycetoma in both cases. Following the excisions, Madurella mycetomatis was identified as the causative organism through culture and PCR analysis. Due to the lack of response to posaconazole, a switch back to itraconazole was made. Post-surgical management included wound care with VAC therapy and biomatrix grafting, resulting in notable improvement in wound healing. The patient’s treatment course has now extended for more than five years, highlighting the prolonged duration of the disease. This case emphasizes the challenges of managing eumycetoma, particularly in recurrent cases where treatment failure occurs. The integration of surgical and systemic antimycotic approaches is critical for managing persistent mycetomas, and frequent monitoring of both systemic drug therapy and wound healing is essential to achieve optimal outcomes.