Building monitoring and protection are important components of underground projects in urban areas. Typically the procedures applied for the assessment of settlement-induced damage to buildings are based on simplified assumptions that do not take into account soil–structure interaction. Assessment methods based on the relative stiffness between the structure and the soil exist, but they are rarely applied in practice due to concerns about the accuracy and reliability. The primary aim of this work is to use the large amount of monitoring data provided by the Crossrail project in London to improve understanding of building performance and existing damage assessment methods. The paper gives an initial overview of the available monitoring data by presenting four representative case studies for load-bearing masonry buildings on shallow foundations. Structural data are then used to evaluate the consistency of predictions produced by different relative stiffness formulations. The results show the effect of building stiffness on the soil surface settlements and clarify the effects of various assumptions made during prediction. The conclusions highlight opportunities to improve prediction procedures and the need for more detailed monitoring data for future tunnelling projects.