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Controlling building displacements induced by tunnelling is a major issue in densely urbanised areas, particularly for listed heritage structures. Major tunnelling projects provide opportunities to assess the ability of advanced numerical models to address this issue, in conjunction with the large amount of monitoring data that are gathered during the works. This paper considers the case of two Grade-I listed buildings (St. Mary Abchurch and Mansion House) affected by the Bank Station Capacity Upgrade in London (UK) where complex excavation works were conducted to improve the existing underground infrastructure. Both conventional and innovative monitoring was carried out to control the effect of tunnel construction on these buildings. Following the works, three-dimensional finite element analyses were conducted by adopting a semi-coupled modelling approach. In these analyses, the pre-existing damage in the buildings prior to tunnelling has been considered by adjusting the properties of embedded solids that are used to idealise the structure. The analyses also considered salient aspects that are often neglected in routine risk-assessment procedures, such as the excavation modelling sequence covering both pilot tunnelling and enlargement, the skew building-tunnel alignment, and the effect of closely spaced tunnel excavations on surface ground deformations. The results highlight the challenges associated with idealising historic structures with semi-coupled models; nevertheless, they encourage the integrated use of innovative monitoring systems and advanced numerical modelling as a tool to control the process of tunnel excavation in complex urban environments.