Structural deformation monitoring is crucial for the identification of early signs of tunnelling-induced damage to adjacent structures and for the improvement of current damage assessment procedures. Satellite multi-temporal interferometric synthetic aperture radar (MT-InSAR) techniques enable measurement of building displacements over time with millimetre-scale accuracy. Compared to traditional ground-based monitoring, MT-InSAR can yield denser and cheaper building observations, representing a cost-effective monitoring tool. However, without integrating MT-InSAR techniques and structural assessment, the potential of InSAR monitoring cannot be fully exploited. This integration is particularly demanding for large construction projects, where big datasets need to be processed. In this paper, we present a new automated methodology that integrates MT-InSAR-based building deformations and damage assessment procedures to evaluate settlement-induced damage to buildings adjacent to tunnel excavations. The developed methodology was applied to the buildings along an 8-km segment of the Crossrail tunnel route in London, using COSMO-SkyMed MT-InSAR data from 2011 to 2015. The methodology enabled the identification of damage levels for 858 buildings along the Crossrail twin tunnels, providing an unprecedented number of high quality field observations for building response to settlements. The proposed methodology can be used to improve current damage assessment procedures, for the benefit of future underground excavation projects in urban areas.