Despite the fact that the use of eye drops preparations is a simple task for most of the people for certain patients (i.e. for elderlies or for those suffering by musculoskeletal or neurological diseases) can make the eye drop insertion rather problematic. Given that most of the ocular diseases are associated with age, the poor patient compliance with the treatment is a common issue. Thus, for the design of the eye drop vials, the aforementioned issue should be taken into account and reliable methods for the description of their squeezability behavior should be developed. The present study aims both to develop prototype instrumentation and to fully determine the squeezability behavior of five different pharmaceutical eye-droplets vials. The correlation between the force required to deliver each droplet and the time is also investigated. Five different eye drops vials (containing different commercial available ophthalmic preparations) were selected to be investigated. Squeezability tests were performed using prototype instrumentation. A linear correlation between the applied force and the time was proven; a sudden decrease in the required force when each drop released was observed. The squeezability factor in all cases is below the typical range for the human squeezability requirements and is a combination of the liquid and the vial parameters.