Shield tunnelling using pressurized face Tunnel Boring Machine (TBM), such as Earth Pressure Balance (EPB) and slurry shields, generally allows good control of surface settlement. In a normal tunnelling environment, when the applied operating face pressure is lower than the mobilized earth pressure, the ground moves towards the TBM face, leading to positive face loss and surface settlement. Conversely, in a scenario of negative face loss, where the face pressure exceeds the mobilized earth pressure, the ground is pushed away, causing subsurface ground movement away from the TBM face and resulting in heave at the surface. This paper presents a case history detailing field observations of building responses to tunnelling underneath. Two buildings, one featuring with a simple structure on shallow foundations and the other a mid-rise apartment supported on piled foundations, were extensively instrumented with building settlement markers, tiltmeters, and optical prisms for close monitoring during tunnel advancement. The results of instrumentation monitoring are thoroughly discussed alongside recorded TBM driving data. The observed outcomes are consistent with the negative face loss tunnelling approach and are documented for future reference in similar projects.