Perennial ryegrass (PRG, Lolium perenne L.) breeding effort in New Zealand (NZ) has increased since c. 1990, resulting in greater functional trait diversity (e.g. heading date, ploidy, and associated Epichloë endophyte strain) in commercial products. This study quantified the variation, associations and interactions in dry matter (DM) yield, nutritive value and persistence‐related traits among commercial cultivar‐endophyte combinations released between 1973 and 2012, as a basis for assessing gains in value being delivered to the pasture‐based livestock industries. Twenty‐four or 28 combinations were compared over 3 years in two trials in each of two regions: Waikato in northern NZ (dryland), and Canterbury in central eastern South Island (irrigated). Cultivar‐endophyte combinations were sown in mixtures with white clover, and pastures were intensively grazed 8–11 times per year by dairy cows. Principal Component Analysis identified 4 distinct clusters for the DM yield variables and for metabolisable energy (ME) content in each of the four trials. A broadly‐adapted group of three late‐season flowering, AR37‐infected diploids with NZ and Spanish breeding backgrounds dominated the highest‐yielding clusters. Tetraploids dominated the high ME content clusters. Interactions with region were observed throughout the data set: the strongest of these was driven by endophyte strain effects in Waikato. High‐yielding cultivar‐endophyte combinations in these trials were also generally high‐yielding in the standard cultivar merit testing system operated in New Zealand, as interpreted via the DairyNZ Forage Value Index. However, alignment was poorer for medium‐ and lower‐yielding cultivar‐endophyte combinations. Several implications for forage evaluation methods and end‐user industries are identified.