A pill crushing apparatus for use with first and second nestable cups includes a first stage of operation wherein a first cup holder is moved linearly toward a second cup mounting surface holding a second cup and a second stage of operation wherein the first cup holder rotates relative to the rotationally fixed second cup. During the first stage of operation, the pills first may begin to crush against the linear load being applied thereto, and thereafter grind into a fine powder due to the rotational force of the first cup against the second cup.