In temperate pasture-based dairy systems, ryegrass (Lolium perenne L.) is a key forage due to its high crude protein (CP) content, yet its rapid ruminal degradation could limit the supply of rumen-undegraded protein and essential amino acids (EAAs) to dairy cows. This study aimed to investigate the in situ ruminal degradability of CP and individual amino acids (AAs) in fresh ryegrass at the vegetative stage. Three second-parity, rumen-cannulated Holstein Friesian cows (487 kg body weight, 16.5 kg milk/day) were used for the incubation of ryegrass samples collected in different seasons at the vegetative stage. The degradation kinetics were assessed using the Ørskov and McDonald model, with mathematical corrections for microbial contamination. Results showed that the effective degradability (ED) of AAs was generally higher than that of CP (p < 0.05), exceeding 2%, and that some EAAs, particularly lysine, exhibited an ED up to 5.5% greater than CP (p < 0.05). These differences underscore the need for caution when using CP as a proxy for AA degradation in dietary formulations. Given the high degradability of ryegrass AAs, it would be important to monitor and adjust their supply in diets with high ryegrass inclusion to prevent potential deficiencies that could impair milk production and reduce feed efficiency.