A fishing reel winding apparatus for use with a fishing reel includes a spool-retaining structure in which a spool is mounted and the spool connects to a spool handle hub from which a spool winding handle radially extends for removably interconnecting a fishing reel winding handle and the chuck of an electric drill, so that operation of the electric drill rotates the chuck and the reel to wind fishing line onto the spool, the fishing reel winding apparatus including: a chuck gripping stem for insertion into and engagement by a drill chuck and a handle hub engagement assembly drivably connected to the chuck gripping stem. The handle hub engagement assembly preferably includes a hub receiving cup having a cup side wall with a lateral handle receiving notch and a cup bottom wall drivably connected to the chuck gripping stem.