A diamond special-shaped grinding wheel includes an upper base body, a lower base body, and a grinding ring. The upper base body is disposed at the upper end of the lower base body, and the upper base body and the lower base body are fixedly connected to form a grinding wheel body. The grinding ring is fixed to an outer ring of the grinding wheel body; the grinding wheel body is internally provided with one or two annular grooves communicated with the upper end face of the grinding wheel body. A plurality of mixed flow channels is formed in the grinding ring. One end of each mixed flow channel extends to an annular grinding opening of the grinding ring, the other end is communicated with one annular groove, and the annular grooves are communicated with an external negative pressure air source device. Also disclosed is a vertical machining cooling system.