Background: With the improvement of healthcare, the number of elderly individuals, including those with obesity, is increasing. The accumulation of various ventilation problems associated with the use of face masks in both these patient groups can pose a challenge even for an experienced anesthesiologist. The main aim of this study was to evaluate the ventilation of elderly patients with obesity using face masks, uncuffed or cuffed, and compare it with values obtained among patients with obesity who are not elderly. The secondary aim of the study was to demonstrate which of the two masks tested is better for elderly patients with android and gynoid obesity. Methods: This study was conducted at University Clinical Hospital No. 1 in Lodz among 108 patients with obesity, 50 elderly and 58 non-elderly. Patients’ BMIs ranged from 35.0 to 59.0. For the study, the uncuffed Intersurgical Eco Mask II and cuffed Ambu Ultra Seal face masks were used. Expiratory tidal volume and leakage obtained during the use of both types of masks were examined. The obtained data were analyzed using the Kolmogorov–Smirnov test and supplemented with Wilcoxon test values. Results: In elderly patients with obesity, especially those with gynoid obesity, the use of the Intersurgical Eco Mask II is associated with better ventilation parameters than the Ambu Ultra Seal mask. Only in the case of elderly patients with android obesity did the use of the Ambu Ultra Seal mask yield similar results to the Intersurgical Eco Mask II. Conclusions: Uncuffed face masks provide better ventilation parameters during manual bag ventilation in elderly patients with obesity.