The use of ‘cut-and-carry’ (the mechanical harvesting and feeding of fresh grass) has increased in some temperate regions in recent years and evidence suggests that sward management practices in this system differ to conventional grazing. In order to investigate this further, a 2 × 3 × 2 factorial experiment was used to examine the effect of low (1489 kg dry matter (DM)/ha; LHM) and high (2142 kg DM/ha; HHM) pre-cutting herbage mass; three ryegrass cultivars, diploid perennial ryegrass (Lolium perenne; DIP), tetraploid perennial ryegrass (TET) and a hybrid ryegrass (Lolium multiflorum × L. perenne; HY); and the inclusion of red clover (Trifolium pratense) on sward herbage production, nutritive value and ryegrass morphology. Plots were harvested according to herbage mass from March to November in 2018 and 2019. Annual DM production was 1489 kg DM/ha higher in HHM than in LHM swards. Pre-cutting herbage mass had no effect on organic matter digestibility (OMD) in early season for DIP and TET swards or in late season for all cultivars. There was an interaction between ryegrass cultivar and clover inclusion in annual yield whereby red clover increased DM production in all cultivars however, its effect was largest in HY swards. Red clover inclusion increased DM production but reduced OMD in early and mid-seasons. Overall, TET swards were lowest in neutral detergent fibre and highest in OMD compared to HY and DIP. Pre-cutting herbage mass, ryegrass cultivar and red clover inclusion require careful consideration when establishing and managing pastures in cut-and-carry systems.