From 2002 to 2006, longwall mining was undertaken directly beneath the Cataract Tunnel, which is a 100-year-old, heritage-listed tunnel in Hawkesbury Sandstone responsible for delivering 20 per cent of Sydney's annual water supply. At one location, undermining resulted in movement of at least 350 mm along a known fault that transects the tunnel. During this movement, the continued operation of the tunnel was ensured through a careful system of planning, monitoring and management.Of key importance to the success of the operation was the use of advanced numerical modelling to guide operations at all levels, including feasibility assessment, pre-mine mitigation works, monitoring design, operation performance and post-mining condition. This allowed many aspects of the potential impacts to be explored, including joint movements, rock mass deformations and changes in permeability. A key challenge was to successfully model near-field influences on adverse geological structure due to very far-field effects. This paper explains the model's conceptual development, calibration, performance and limitations.Modelling provided the confidence to manage the impacts of large mining-induced movement on key infrastructure and ultimately predicted fault movement accurately. The fault movement remains one of the highest ever recorded due to mine subsidence.CITATION:Swarbrick, G, Sullivan, T J and Pinkster, H, 2014. Longwall mining beneath critical infrastructure - prediction versus performance of the Cataract Tunnel, New South Wales, Australia, in Proceedings AusRock 2014: Third Australasian Ground Control in Mining Conference , pp 157-166 (The Australasian Institute of Mining and Metallurgy: Melbourne).