An oil filter removal and drain system including an oil-filter-removal assembly and a drain-attachment assembly in functional combination. The oil-filter-removal assembly includes a top-frame, a bottom-frame, a geared-socket-hub, a filter-socket, a plurality of geared-clamp-jaws, a filter-gasket, and a toggle-clamp in functional and structural combination. The drain-attachment assembly includes a drain-attachment-body, a drain-toggle-clamp, a drain-nipple, and a filter-cutter. The drain-attachment assembly is removably affixable to the oil-filter-removal assembly via the plurality keyhole-stud-receivers of the drain-attachment assembly accepting and retaining the plurality of keyhole-studs of the oil-filter-removal assembly. An oil-filter-removal assembly may be used on many different types of fluid filters (e.g., hydraulic fluid, diesel fuel, engine oil, etc.).