This paper presents galloping analysis of multiple-degree-of-freedom (MDOF) structural roofs with multiple orientations. Instead of using drag and lift coefficients and/or their combined coefficient in traditional galloping analysis for slender structures, this study uses wind pressure coefficients for wind force representation on each and every different orientation roof, facilitating the galloping analysis of multiple-orientation roof structures. In the study, influences of nonlinear aerodynamic forces are considered. An energy-based equivalent technique, together with the modal analysis, is used to solve the nonlinear MDOF vibration equations. The critical wind speed for galloping of roof structures is derived, which is then applied to galloping analysis of roofs of a stadium and a high-rise building in China. With the aid of various experimental results obtained in pertinent research, this study also shows that consideration of nonlinear aerodynamic forces in galloping analysis generally increases the critical wind speed, thus enhancing aerodynamic stability of structures.