The ancient Chinese calligraphy, which employs the Han characters for artistic display, has enjoyed a predominant position in Chinese art. Calligraphy has twofold purposes: one is for practical use and the other is for aesthetic appreciation. Writers’ psychology and personality can be manifested through usage of pen-and-ink. The unique visual appeal and feeling had ancient rulers and intellectuals valuing it as fundamental enculturation of a person. The calligraphy of Han characters has over the past few millennia developed into a highly mature system of aesthetic appreciation. Ancient Chinese men of letters, based on the backbone of calligraphy, identified the so-called eight strokes of the character Yong, including dot, horizontal, erect, hook, raise, curve, throw and pressing forcefully. This classification has had tremendous influence on Chinese calligraphers of later generations. Based on the eight principles, the paper invites modern calligraphers to compare and analyze the works of eleven calligraphers of the Ming Dynasty and the Qing Dynasty. The GM(0,N) model is employed for sorting. This study objectively interprets the value of calligraphic works in terms of an innovative mathematical assessment method. It looks forward to a rational-kansei future of art development and cross-disciplinary interflow.