Large old trees are disproportionate providers of structural elements (e.g. hollows, coarse woody debris), which are crucial habitat resources for many species. The decline of large old trees in modified landscapes is of global conservation concern. Once large old trees are removed, they are difficult to replace in the short term due to typically prolonged time periods needed for trees to mature (i.e. centuries). Few studies have investigated the decline of large old trees in urban landscapes. Using a simulation model, we predicted the future availability of native hollow-bearing trees (a surrogate for large old trees) in an expanding city in southeastern Australia. In urban greenspace, we predicted that the number of hollow-bearing trees is likely to decline by 87% over 300 years under existing management practices. Under a worst case scenario, hollow-bearing trees may be completely lost within 115 years. Conversely, we predicted that the number of hollow-bearing trees will likely remain stable in semi-natural nature reserves. Sensitivity analysis revealed that the number of hollow-bearing trees perpetuated in urban greenspace over the long term is most sensitive to the: (1) maximum standing life of trees; (2) number of regenerating seedlings ha(-1); and (3) rate of hollow formation. We tested the efficacy of alternative urban management strategies and found that the only way to arrest the decline of large old trees requires a collective management strategy that ensures: (1) trees remain standing for at least 40% longer than currently tolerated lifespans; (2) the number of seedlings established is increased by at least 60%; and (3) the formation of habitat structures provided by large old trees is accelerated by at least 30% (e.g. artificial structures) to compensate for short term deficits in habitat resources. Immediate implementation of these recommendations is needed to avert long term risk to urban biodiversity.