In this study, we perform two-scale damage/strength analysis of carbon fiber-reinforced plastics (CFRP) that explicitly takes into account the randomness of fiber distribution. This analysis is conducted by combining a two-scale analysis method based on a homogenization theory with the Hoffman’s damage determination criterion. To consider the randomness of fiber distribution, several unit cell models with random fiber distribution are prepared as microscopic models. Then, they are randomly assigned at integration points in a macroscopic model of CFRP to perform two-scale damage/strength analysis. The effects of random fiber distribution on the damage and strength properties of [0]4 and [90]4 unidirectional CFRP and a [0/90]s cross-ply CFRP are investigated by comparing the results with and without considering the randomness of fiber distribution, where the numbers in [] denote the fiber orientation angles, and the subscripts 4 and s respectively indicate the number of plies and the symmetric lamination. It is confirmed that the effects of random fiber distribution for [0]4 are relatively small, whereas those for [90]4 are remarkably large; the strength of [90]4 with random fiber distribution becomes about 32% lower than that without randomness. In the case of [0/90]s, initial damages are observed at quite lower stress levels when the randomness of fiber distribution is considered.