High-performance fibers are well-known for their high stiffness and strength under axial tension. However, in their many applications as critical components of textiles and composites, transverse loads widely exist in their normal service life. In this study, we modified a micro material testing system to transverse load single fibers using round-head indenters. By integrating the loading platform with the Scanning Electron Microscopy (SEM) operating at a low-vacuum mode, we visualized the failure processes of fibers without conductive coatings. Post-fracture analysis was conducted to provide complementary information about the fibers’ failure. The energy dissipation was compared with the axial tensile experiments. Three inorganic and two organic fibers were investigated, namely carbon nanotube, ceramic, glass, aramid, and ultrahigh molecule weight polyethylene fibers. Different failure characteristics were reported. It is revealed that the organic fibers had higher energy dissipation than the inorganic fibers under the transverse loading by the round-head indenters. The fiber’s energy dissipation under transverse loading was no more than 17.9% of that subjected to axial tension. Such a reduced energy dissipation is believed to be due to the stress concentration under the indenter. It is suggested that the fiber’s material constituent, structural characteristics, and stress concentration under the indenter should be considered in the fiber model for textiles and composites.