Drought is one of the most typical and serious natural disasters, which occurs frequently in most of mainland China, and it is crucial to explore the evolution characteristics of drought for developing effective schemes and strategies of drought disaster risk management. Based on the application of Cloud theory in the drought evolution research field, the cloud transformation algorithm, and the conception zooming coupling model was proposed to re-fit the distribution pattern of SPI instead of the Pearson-III distribution. Then the spatio-temporal evolution features of drought were further summarized utilizing the cloud characteristics, average, entropy, and hyper-entropy. Lastly, the application results in Northern Anhui province revealed that the drought condition was the most serious during the period from 1957 to 1970 with the SPI12 index in 49 months being less than −0.5 and 12 months with an extreme drought level. The overall drought intensity varied with the highest certainty level but lowest stability level in winter, but this was opposite in the summer. Moreover, drought hazard would be more significantly intensified along the elevation of latitude in Northern Anhui province. The overall drought hazard in Suzhou and Huaibei were the most serious, which is followed by Bozhou, Bengbu, and Fuyang. Drought intensity in Huainan was the lightest. The exploration results of drought evolution analysis were reasonable and reliable, which would supply an effective decision-making basis for establishing drought risk management strategies.