We developed an automatic laser-to-optical-fiber coupling (ALOC) system that is based on the difference in the Raman scattering signals of the core and cladding of the optical fiber. This system can be easily applied to all fields of fiber optics since it can perform automatic optical coupling within a few seconds regardless of the core size or the condition of the output end of the optical fiber. The coupling time for a commercial single-mode fiber for a wavelength of 632.8 nm (core diameter: 9 μm, cladding diameter: 125 μm) is ∼1.5 s. The ALOC system was successfully applied to single-mode-fiber Raman endoscopy for the measurement of the Raman spectrum of carbon nanotubes.