Context Improving the stability of legumes in grasslands in the face of variable seasonal conditions is key to mitigating risks posed by drought. Aims We assessed the persistence of a range of legume species and cultivars in order to inform legume choice for pasture improvement and identify priority species for further development. Methods Twenty field experiments in four series were conducted at sites with contrasting seasonal and soil characteristics in the ‘high-rainfall’ (560–920 mm long-term average) Tablelands and Monaro regions of New South Wales, Australia. Legumes were grown as pure swards and assessed periodically for seedling density, plant frequency and dry matter for up to 5 years. Key results Legume dry matter production was positively correlated with plant frequency. However, most legumes persisted poorly at most sites, particularly on soils of lower fertility. Subterranean clover (Trifolium subterraneum) cv. Goulburn was the best performing cultivar of that species across sites on the Southern Tablelands and Monaro. Yellow serradella (Ornithopus compressus) cvv. Avila and Yellotas showed promising persistence, particularly under drought conditions. White clover (T. repens) was the most broadly adapted of the perennial legumes across a range of soils, but persistence was still inadequate at many sites. Lucerne (Medicago sativa) was approximately twice as productive as the next-most productive species when soil conditions suited its growth, but it failed to persist on acidic, low-fertility soils. Conclusions Serradella species (yellow and French, O. sativus) and white clover, in conjunction with subterranean clover, offer the best near-term prospects for diversifying legume productivity and resilience under variable seasonal conditions in tableland environments. Implications An increased focus on phenology and seed characteristics is suggested to improve the persistence of annual and facultative perennial legume species in grasslands. Serradella and white clover are identified as the highest priorities for cultivar development for tableland environments of south-eastern Australia.