Aspergillus tracheobronchitis and Aspergillus empyema are two rare manifestations of Aspergillus infection. This case report presents a patient with chronic obstructive pulmonary disease who developed a pseudomembranous Aspergillus tracheobronchitis, bronchopleural fistula and empyema 16 months after lobectomy for an aspergilloma. Bronchoscopy proved to be important for assessment of severity. Combined systemic anti-fungal treatment (voriconazole) and open window thoracostomy were used to successfully treat the patient.