We report the case of a 60-year-old Caucasian Greek woman who sustained TPP with hemopneumothorax due to a blunt chest trauma after a traffic accident. She was a nonsmoker and had a history of diabetes mellitus type II, coronary disease, and heart failure class III. On physical examination, she was hemodynamically stable and well perfused. Auscultation of the lungs revealed decreased respiratory sounds over her right hemithorax, and painful right shoulder motions were noted. Her white blood cell count was 15.6×103/μL, and there were mild increases in serum transaminase, creatine phosphokinase, and lactic dehydrogenase activity. The chest X-rays were consistent with bilateral parenchymal contusion and showed fractures of the fifth and sixth ribs on the right and also showed a cavitary lesion with an air-fluid level in the basal segment of the right lower lobe. Our patient was admitted to the surgical ward. In the control CT taken 24 hours after admission, a low-percentage pneumothorax and a thin-walled air cavity were detected on the anterior segment of the right lower lobe in close contact with the interlobar fissure. Also, there was evidence of an extensive contusion in the posterior and lateral segments of the right lower lobe, and the presence of air was demonstrated. This finding was attributed to an early sign of a second cavitation. During the period between the first and second CT scans, the control was performed with the use of conventional chest X-rays, as it was ordered by the clinicians. Pneumothorax was treated, and the findings of a CT evaluation about one month later showed complete resolution of the air-filled cavitary lesion anteriorly, while in the area of the contusion a large thin-walled air cavity displaying an air-fluid level was evident. These findings were consistent with TPP. Additional findings were right pleural effusion and pericardial effusion, which were attributed to heart failure. Our patient was treated conservatively with antibiotherapy. She was asymptomatic thereafter, and the second TPP was completely resolved six months later, as was proven by a follow-up CT scan.