Postswallow pharyngeal pooling may be a risk factor for tracheal aspiration. However, limited literature shows the potential association between pharyngeal pooling and aspiration in head and neck cancer (HNC) patients. This study investigates the relationship between postswallow pharyngeal pooling and aspiration in HNC patients with oropharyngeal dysphagia. Furthermore, the effects of tumor stage, tumor location, and cancer treatment on aspiration were examined. Ninety dysphagic HNC patients underwent a standardized fiberoptic endoscopic evaluation of swallowing (FEES) using thin and thick liquid boluses. For each swallow, three visuoperceptual ordinal variables were scored: postswallow vallecular pooling, postswallow pyriform sinus pooling, and aspiration. Logistic regression analyses with correction for the location of pooling, tumor stage, tumor location, and cancer treatment were performed to explore the association between pooling and aspiration. No significant association was found between postswallow vallecular pooling and aspiration for thin liquid. However, severe versus mild-to-moderate postswallow vallecular pooling of thick liquid was significantly associated to aspiration. Similar results were seen after correction for the presence of pyriform sinus pooling, tumor stage, tumor location, or type of cancer treatment. This study showed a significant association between severe postswallow pyriform sinus pooling of thick liquid and aspiration, independent of the presence of vallecular pooling, tumor stage, tumor location, or cancer treatment. Concluding, location (valleculae versus pyriform sinuses), liquid bolus consistency (thin versus thick liquid), and amount of postswallow pharyngeal pooling (no pooling, mild/moderate pooling, severe pooling) have an influence on the probability of aspiration in dysphagic HNC patients, and they should be carefully considered during FEES, even in the absence of aspiration during the examination.