Chronic pulmonary aspergillosis can present in four distinct clinical syndromes, one of which is chronic cavitary pulmonary aspergillosis (CCPA). CCPA is generally associated with a mildly immunosuppressed state or, in immunocompetent patients, with structural lung damage. Severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) infection has been associated with reactivation of previous quiescent infections such as tuberculosis and invasive fungal infections, but CCPA in a patient with COVID-19 is rarely reported. Here we present the case of a 57-year-old man with CCPA associated with COVID-19 infection in whom latent aspergilloma was most likely activated after SARS-CoV-2 infection. The patient presented with severe COVID and, after initial response to treatment, started to deteriorate due to reactivation of latent aspergilloma to a more aggressive CCPA form. After confirmation of the diagnosis, the patient was initiated on treatment with voriconazole. He showed a good response to treatment with clinicoradiological response. This case also depicts one of the common causes of clinical deterioration in otherwise recovering COVID-19 patients.