Background: A comparison of panoramic radiography (PAN) alone and PAN together with small field of view cone beam computed tomography (sFOV-CBCT) for diagnosis of symptomatic pathologies of the maxillary sinus was carried out by clinicians of different experience. Methods: Corresponding radiographic images (PAN/sFOV-CBCT) of 28 patients with symptomatic maxillary sinus pathologies were chosen and analyzed by two general practitioners (GP), two junior maxillofacial surgeons (MS1), and three senior maxillofacial surgeons (MS2) via questionnaire. Results: Visibility of maxillary pathologies in PAN was significantly different between the groups (GP 39%, MS1 48%, MS2 61%; p < 0.05). The number of incidental findings varied within examiner groups in PAN with a significant increase in MS2 (p = 0.027). The majority of examiners rated an additional sFOV-CBCT as "reasonable"/ "required" with a significant influence of the examining groups (GP 98.2%, MS1 94.6%, MS2 80.9%; p = 0.008). In 58% of cases, an additional sFOV-CBCT was seen as "affecting therapy" with significant differences between the groups (GP 68%, MS1 50%, MS2 55%; p < 0.001). Conclusions: PAN alone is not sufficient for the evaluation of pathologies of the maxillary sinus. But, depending on the examiners' clinical experience, it remains a useful diagnostic tool. Along with the observers' training, significant benefits of an additional sFOV-CBCT for evaluation of symptomatic maxillary sinus pathologies were detected.