Three perennial ryegrass cultivars, early (Gremie), intermediate (Morenne) and late (Perma) maturity, were each sown as monocultures in eight identical groups. These 'groups' were sequentially taken for first silage cuts at 10-day intervals, with second cuts after 6 weeks followed by further cuts to the end of the season. The work was repeated in 3 different years. Delaying the first cut increased dry matter (DM) and digestible organic matter (DOM) yields, despite a lowered percentage of digestible organic matter in the dry matter (DOMD), but caused reduced DM and DOM yields at the second cut even though DOMD increased. Therefore, large fluctuations in DM yield were recorded but, due to the counterbalancing effect of DOMD, the DOM yield responses were less extreme. No significant effects on productivity due to varying timing of the first cut were recorded beyond the second cut. Maturity differences between cultivars caused similar responses as varying cutting times. Absolute losses in DM yield incurred by early cutting were not fully compensated by the enhanced regrowth rates to the second cut. Cutting early to obtain two cuts within the time period for one late first cut increased yields during that period. However, this advantage was lost due to lower yields at the following cuts. Avoiding cutting at too immature or mature a growth stage, coupled with selection of cultivars of specific maturities to allow flexibility in timing of cutting, was generally the best strategy for optimising the herbage yield/quality balance in both the first and second silage harvests.