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Management of fungal empyema secondary to an oesophagopleural fistula remains challenging, especially when primary closure of the fistula is delayed. Prolonged infection causes malnutrition and, in rare cases, pleurocutaneous fistula (PCF) formation. We report the case of a woman in the mid-40s presenting with spontaneous oesophageal rupture complicated by right-sided empyema thoracis. Chest tube thoracostomy was performed, and pleural cultures yielded Candida glabrata, for which micafungin was initiated. Accidental removal of the chest tube resulted in purulent wound discharge, prompting re-admission and concern for PCF. A repeat CT demonstrated persistence of oesophagopleural fistula and empyema, while bronchoscopy excluded bronchopleural connections. Endoscopic clipping of the fistula was attempted but was unsuccessful. A multidisciplinary conference recommended video-assisted thoracostomy once the patient was optimised, while continuing long-term culture-guided antibiotics. Despite these interventions, she developed nosocomial pneumonia with respiratory failure. This case underscores the importance of early fistula closure, adequate pleural drainage and culture-guided antimicrobial therapy for optimal management.