Background/Objectives: Supraglottic airway devices are commonly used airway management tools, with various second-generation laryngeal masks available for patients undergoing general anesthesia. These devices offer improved sealing, gastric suction capabilities, and the potential for tracheal intubation. This study compared the recently introduced Singularity^TM Air laryngeal mask with two well-established devices, Ambu^® AuraGain^TM and i-GEL^®, under clinical conditions. Methods: We prospectively included 98 adult patients scheduled for elective surgery requiring general anesthesia. Patients were randomized to one of three laryngeal mask groups, and data on insertion success, ventilation efficiency, and postoperative complications, such as sore throat and dysesthesia, were collected. The primary endpoint was oropharyngeal sealing pressure, with additional assessments of insertion ease and bronchoscopic glottic visibility. Results: Median initial oropharyngeal leak pressure was lowest with i-GEL^® (22 cm H₂O) as opposed to Ambu^® AuraGain^TM (25 cm H₂O) and Singularity^TM Air (25 cm H₂O) [p = 0.0138], but this difference equalized after 15–30 min. I-GEL^® showed higher insertion success (88%, p = 0.001) and shorter time-to-first ventilation (29 s, p = 0.0106). Conversely, the gastric tube insertion rate was lower (70% versus >90% in the other masks). The Ambu^® AuraGain^TM and Singularity^TM Air performed similarly for most parameters. No significant differences were observed in tracheal intubation potential or postoperative adverse events among the three groups. Conclusions: The Singularity^TM Air performed comparably to Ambu^® AuraGain^TM and i-Gel laryngeal masks in oropharyngeal sealing pressure. I-Gel^® had the highest successful insertion rate. Most of the differences detected were not statistically significant, with all three masks providing effective airway management.