This paper aims to develop a performance measure for underactuated grasping devices, which is useful in making design decisions to obtain an optimally performing device. Underactuated fingers, defined as having more degrees of freedom than degrees of actuation, intrinsically adapt their shape to the object. However, the equilibrium configuration and grasp forces of these fingers are not fully controllable, which may limit their performance. The grasp performance measure defined in this paper consists of three aspects: (1) the ability to grasp objects, which is limited by the equilibrium conditions and constraints of both the underactuated fingers and the freely movable object; (2) the grasp stability, which takes the passive compliance of the fingers into account; (3) the ability to oppose disturbance forces on the grasped object by passively adapting the frictional grasp forces. This measure was applied to optimize a planar grasping device with two underactuated fingers, each consisting of two phalanges, able to grasp freely moving circular objects.