SummaryRestoration of degraded former Cumberland Plain Woodland by planting of native trees and shrubs was undertaken by Greening Australia (NSW) on the Cumberland Plain, west of Sydney, Australia, from the mid‐1990s. Our study examined the success of this restoration in stands of two ages using species composition as the criterion. The starting point (pasture) and the target (reference woodland) were sampled to document the extent of progress of species composition from pasture through young (3–5 years) and old (9–11 years) restoration stands to reference woodland across three sites at two surveys. Comparisons showed restored stands of both ages differed significantly from pasture, and from each other, showing decreasing similarity between the restoration stands and pasture at all sites. Despite this, species composition in restored stands at all three sites was still significantly different from reference sites, showing that none had achieved the target reference state after 11 years. The trajectory of restored sites between the two surveys was not towards the reference state. Restoration resulted in the establishment of 20 (71%) of the planted species. Recruits from five planted species were found. A further 40 unplanted native ground layer species were found in restoration. Structurally, tree cover increased with time since restoration and was higher in the restored sites. Ground cover, which was very high in pasture was lower in some restored sites. The majority of the unplanted native species were resprouters, and their presence in the above‐ground vegetation was most likely by vegetative resprouting from the bud‐and‐tuber bank as ground cover was lower with the increase in tree cover and shade. Tree and shrub planting by itself has not yet progressed the restored areas to the species composition of reference sites. Additional tools will be needed to assist restoration, specifically the addition of re‐seeder native plants not able to persist through vegetative resprouting after restoration. Measures to control the burden of weeds present in the pasture seed bank are also required.