Systems and methods for measuring IOP including a tonometer comprising sensor for detecting corneal contacted area and outputting an indication thereof to an observer to facilitate determination of when an endpoint is reached such that certain area of cornea has been flattened to obtain correct IOP reading. Camera and/or an image sensor can be provided for real-time video streaming or still frame photo imaging of retina as cornea flattens during measurement procedure. Independently of, or in conjunction with, sensing of corneal contact area, real-time or post processing of image data can be performed to determine when the endpoint is reached to obtain correct IOP reading.