Adhesion of a pre-stressed silicone rubber film to a planar graphite surface was investigated by a new cylindrical punch method. A homemade apparatus was constructed to meet force and displacement resolutions of 0.1μN and 10nm. When the punch approached the intersurface force range across the punch-film gap, the film jumped into contact at “pull-in”. Upon unloading, once the tensile load reached a threshold, a spontaneous delamination occurred at “pull-off” with a non-zero contact circle. A theoretical model was constructed based a simple energy balance. The new method can be used to characterize an adhesion interface between a pre-stressed free-hanging film and a rigid substrate.