A cross-recess screwdriver sharpening assembly for sharpening a cross-recess screwdriver includes a housing that has a sharpening aperture. A plurality of grinding wheels is rotatably mounted within the housing. Each of the grinding wheels is arranged to define a grinding space. A plurality of sleeves is included wherein each of the sleeves is removably extendable into the interior of the housing to have the cross-recess screwdriver positioned therethrough such that the cross-recess screwdriver extends into the housing. The sharpening aperture receives one of the sleeves therethrough and is centrally aligned with the grinding space such that the cross-recess screwdriver is extendable into the grinding space to sharpen the cross-recess screwdriver. A drive is mounted in the housing and mechanically coupled to each of the grinding wheels. The drive is turned on to rotate each of the grinding wheels.