We demonstrate the use of combined simultaneous atomic force microscopy (AFM) and laterally resolved Raman spectroscopy to study the strain distribution around highly localised deformations in suspended two-dimensional materials. Using the AFM tip as a nanoindentation probe, we induce localised strain in suspended few-layer graphene, which we adopt as a two-dimensional membrane model system. Concurrently, we visualise the strain distribution under and around the AFM tip in situ using hyperspectral Raman mapping via the strain-dependent frequency shifts of the few-layer graphene's G and 2D Raman bands. Thereby we show how the contact of the nm-sized scanning probe tip results in a two-dimensional strain field with μm dimensions in the suspended membrane. Our combined AFM/Raman approach thus adds to the critically required instrumental toolbox towards nanoscale strain engineering of two-dimensional materials.