Subsidence during shallow tunnels construction can represent a critical aspect when buildings or primary roads are undercrossed. Similar situations are often occurring within the project of modernization of the A1 highway stretch crossing the Apennine between Bologna and Florence. In such cases, a proper monitoring system is necessary to assess the entity of subsidence phenomena, compare them to the design assumptions and try to avoid damages to structures within the subsidence basin. Topographic monitoring of the surface has mainly been adopted to control subsidence phenomena during construction, integrated by extenso-inclinometers where necessary. Data read by the settlement monitoring systems installed during the excavation of 14 different large cross-section tunnels are herein shown, describing the main geological conditions and the excavation and consolidation systems adopted in each case. The obtained subsidence trough shapes are also compared to semi-empirical methods for subsidence prediction, confirming the reliability of traditional approaches assuming a Gaussian curve shape for the transverse settlement trough. The analyzed case histories are gathered in three groups, characterized by almost homogeneous geological conditions, and, for each one of them, reference values of volume loss and shape parameter are derived, to be used in similar situations for subsidence prediction adopting the aforementioned semi-empirical method. On the base of such reference parameters and usual damage classification systems, a simplified approach to preliminarily assess where damages on structures during tunnel excavation can be expected is proposed, as a function of geological conditions and overburden. Finally, procedures to be followed during design and construction to deal with subsidence and related damages induced by tunnel construction are briefly presented.