A tool sharpening assembly (100) suitable for sharpening cutting tools (140,350,366,546,562). In some embodiments, a wedge-shaped port is formed between a rotational first abrasive surface (160,262) and a stationary second abrasive surface (162,264) to sharpen a distal cutting edge (146) of a cutting tool (140,230,546). In other embodiments, a cooling mechanism (136,326,330,334,338) actively draws heat generated during a sharpening operation from a tool (140) and through a tool support structure (170,234,328,332) contactingly supporting the tool, in further embodiments, a rotatable abrasive slotted disc (364) comprises at least one inspection aperture (372) formed from an interior sidewall (390) with upper and lower leading and trailing edges (396,398,400,402) of non-uniform separation distance. In other embodiments, a cylindrical drum abrasive member (572) is provided with an associated stationary support plate (574). In further embodiments, a grinding wheel (580,600) is formed of a substrate (582,602) and a plurality of abrasive layers (584,586,592,612,614) adhered thereto.