A pill crushing apparatus for use with first and second nestable cups comprising a first cup holder which is moved linearly toward a second cup mounting surface holding a second cup. The first cup holder rotates relative to the rotationally fixed second cup. During the crushing process, 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. The first cup and second cup have different sidewall angles to promote pill crushing while inhibiting migration of the crush material to prevent the crushed material from reaching the open gap between the top perimeters of the nesting cups. Each cup includes a plurality of lugs having a curved profile configured to engage respective recesses on the cup holders. Each cup is fabricated through thermoforming or vacuum forming techniques.
