Given the importance of large-scale engineering applications of the superconducting compound Nb3Sn, both its use and performance under certain operating conditions have attracted the interest of applied superconductivity researchers and material scientists for several years now. Huge efforts are directed toward understanding the response to applied loads and predicting fracture damage within their internal microstructure; this is fundamental in the design of superconducting coils and magnets which must meet stringent requirements in terms of maximum thermal and electromagnetic loads. In this paper, the fracture behaviors in polycrystalline Nb3Sn and Nb3Sn filaments with composite structures are investigated using the micromechanical finite element (FE) models with Voronoi tessellation. First, the 2D and 3D Voronoi FE models of the polycrystalline Nb3Sn tensile tests are developed and validated to provide insight into the cracking behavior in the intergranular brittle fracture of polycrystalline Nb3Sn. A cohesive zone model is used to simulate crack propagation at the grain level model including grain boundary zones. It is found that the pre-existing cracks of polycrystals and martensitic phase transformation of grains significantly impact the fracture properties in polycrystalline Nb3Sn. Second, detailed FE models of powder-in-tube (PIT) and bronze route (BR) filaments with Voronoi structures for fracture analysis are then developed on the basis of experimental observations of sectional morphologies. The mechanism of crack initiation and propagation under tensile load have been investigated by analyzing the mechanical properties of each component and the characteristics of multi-scale composite structures of filaments. Furthermore, the damage situation is investigated in PIT filaments undergoing transverse compressive load. The proposed simulation method in this paper can be extended to the fracture and damage analysis of Nb3Sn superconducting wires with different layouts and fabrication processes.