Indoor cooling is preferred during hot summers but unappreciated in cold winters. With this research, we aimed to clarify the cooling performances of roof greening throughout the year and identify the optimum roof greening coverage for the indoor thermal environment in Chenzhou, a city in China with hot summers and cold winters. The layout of buildings, building materials, and local climate data of Chenzhou were collected. The ENVI-met model was applied as the analytical tool after its accuracy was confirmed by a field experiment. The Kriging model was employed to interpret the annual effects of roof greening. The analytical results revealed that in Chenzhou, roof greening reduced indoor temperatures throughout the year, and the higher the coverage of roof greening, the greater the performance of indoor cooling. Moreover, hot climates enhanced the indoor cooling performances of roof greening. From the view of annual thermal perception, the increase in roof greening coverage reduced the duration of warm perceptions throughout the year and extended the perceptions of slightly warm, slightly cool, and cool. Generally, increased roof greening coverage improved the indoor thermal perception in Chenzhou throughout the year. The ENVI-met + Kriging model, an evaluation method of annual cycles, can be used to evaluate the annual performance of roof greening in terms of indoor thermal environment in other climate zones.