Context Data are lacking on the effects of heading date of perennial ryegrass (Lolium perenne L.) on ryegrass persistence. Aim We aimed to determine the impact of heading date on perennial ryegrass persistence. Method Two mid-heading (Samson, Bronsyn) and two late-heading (One50, Rohan) cultivars, infected with Epichloë endophytes (AR37, nea2/6 or standard toxic), were established in a replicated plot study grazed by cattle in a subtropical environment of the upper North Island of New Zealand. Persistence characteristics were quantified at least five times per annum, over 4 years. Key results Late-heading cultivars had higher yield, nutritive value, perennial ryegrass content in pasture dry matter, ground cover and tiller density than mid-heading cultivars. There were large seasonal impacts on all ryegrass characteristics, with a major decline over summer and recovery during late autumn into early spring, with less recovery in the final year. Overall, there was a strong linear decline in ryegrass content measured during spring (2018–21). Conclusions The two late-heading cultivars were more persistent than the two mid-heading cultivars, although persistence declined over 4 years for all cultivars. Implications Results support industry recommendations of choosing late-heading cultivars for improved pasture quality and persistence.