Cartilage conduction is known widely as a third hearing transmission mechanism after the air and bone conduction methods, and transducers dedicated to the production of cartilage conduction sounds have been developed by several Japanese companies. To estimate the acoustic performance of the five cartilage conduction transducers selected for this study, both airborne sounds and cartilage conduction sounds were measured. Airborne sounds can be measured using a commercial condenser microphone; however, cartilage conduction sounds are impossible to measure using a conventional head and torso simulator (HATS), because the standard-issue ear pinna simulator cannot reproduce cartilage conduction sounds with the same spectral characteristics as the corresponding sounds measured in humans. Therefore, this study replaced the standard-issue simulator with a developed pinna simulator that can produce similar spectral characteristics to those of humans. The HATS manipulated in this manner realized results demonstrating that transducers that fitted the entrance to the external auditory canal more densely could produce greater cartilage conduction sounds. Among the five transducers under test, the ring-shaped device, which was not much larger than the entrance to the canal, satisfied the spectral requirements.