This paper describes the effects of the elastic modulus and sliding velocity on the friction and shear fracture of smooth silanized rigid disks rotating against thin confined films of poly(dimethylsiloxane) (PDMS) elastomers. A rigid glass disk is rotated against thin PDMS films of different thicknesses and moduli bonded to a glass plate at various speeds. While the disk rotates on the PDMS coated glass plate, a load cell measures the resulting force with a cantilever beam. One end of the cantilever beam is glued to the glass plate, while its other end presses against a load cell. From the balance of forces and torques, the friction force at a given slip velocity is determined. The friction force increases with the slip velocity sublinearly, which is consistent with the results reported previously by Vorvolakos and Chaudhury (Langmuir 2003, 19, 6778). During rotation, however, the glass disk comes off the PDMS film when the shear stress reaches a critical value. This critical shear stress increases with the modulus of the film, but it decreases with its thickness, following a square root relationship, which is similar to the adhesive fracture behavior in thin films under pull-off conditions. A simple model is presented that captures the essential physics of the fracture behavior under shear mode.