Background: When a rescuer walks alongside a stretcher and compresses the patient’s chest, the rescuer produces low-quality chest compressions. We hypothesized that a stretcher equipped with wing boards allows for better chest compressions than the conventional method. Methods: In this prospective, randomized, crossover study, we enrolled 45 medical workers and students. They performed hands-on chest compressions to a mannequin on a moving stretcher, while either walking (the walk method) or riding on wings attached to the stretcher (the wing method). The depths of the chest compressions were recorded. The participants’ vital signs were measured before and after the trials. Results: The average compression depth during the wing method (5.40 ± 0.50 cm) was greater than during the walk method (4.85 ± 0.80 cm; p < 0.01). The average compression rates during the two minutes were 215 ± 8 and 217 ± 5 compressions in the walk and wing methods, respectively (p = ns). Changes in blood pressure (14 ± 11 vs. 22 ± 14 mmHg), heart rate (32 ± 13 vs. 58 ± 20 bpm), and modified Borg scale (4 (interquartile range: 2–4) vs. 6 (5–7)) were significantly lower in the wing method cohort compared to the walking cohort (p < 0.01). The rescuer’s size and physique were positively correlated with the chest compression depth during the walk method; however, we found no significant correlation in the wing method. Conclusions: Chest compressions performed on the stretcher while moving using the wing method can produce high-quality chest compressions, especially for rescuers with a smaller size and physique.