Numerical simulation by finite element analysis was used to investigate the relationship between the strength of glass fiber reinforced plastic (GFRP) and fiber length. Load speed dependability was also investigated, since thermoplastic resin used for GFRP exhibits much nonlinear stress-strain behavior and strong dependency on load speed. For this purpose, we conducted a periodic-cell simulation to address the effect of composite microstructure, matrix viscoplasticity, and microscopic damage (fiber break and matrix crack). When the fiber length was varied, the damage pattern was divided into two patterns: fiber-avoiding propagation and fiber-breaking modes of the matrix crack from fiber ends. When the matrix crack easily propagated in a fiber-avoiding way for shorter fiber lengths, the rate-dependent effect of the matrix was significant. Moreover, we considered the length at which the fracture mode changed based on this analysis, and compared it with the conventional critical length given by Kelly. Since the conventional critical length does not ensure improved composite strength, the consideration of the damage mode transition is essential for selecting the appropriate fiber length for strength improvement.