Background: Despite the availability of contouring guidelines and advanced imaging modalities, interobserver variability (IOV) in the delineation of the planning target volume and organs at risk remains a critical factor influencing treatment quality in radiotherapy. The aim of this study was to examine variations in contour delineation with respect to anatomical landmarks, as well as differences in the inclusion of lymph node levels within the PTV. Methods: Ten senior radiation oncologists from six different institutions participated in the study and contoured PTV1, PTV2 and 16 OARs in a patient with oropharyngeal carcinoma. Interobserver variation was quantified by volume statistics such as mean, standard deviation (SD) and ranges, as well as using coefficient of variance (CoV) and conformity index (CI). Results: High agreement was observed in the inclusion of the ipsilateral lymph node levels Ib–IVa and VIIa+b, whereas notable discrepancies were identified in the delineation inclusion of the cervical triangle group and lateral supraclavicular nodes. Regarding OARs, the greatest variability was observed in the delineation of the left and right inner ear, with volume ranges of 0.12–2.84 cm3 and 0.11–2.38 cm3, respectively. Conclusions: This study reaffirms the presence of significant interobserver variability in the delineation of PTVs and OARs in patients with oropharyngeal carcinoma. Especially inclusion of elective lymph node levels and definition of margins around the gross tumor volume are substantial factors for IOV. By emphasizing structured anatomical assessment as a standard approach, variability can be minimized, treatment consistency enhanced, and ultimately, patient outcomes improved.