Two-dimensional (2D) semiconductors are one of the most extensively studied modern materials showing potentials in large spectrum of applications from electronics/optoelectronics to photocatalysis and CO2 reduction. These materials possess astonishing optical, electronic, and mechanical properties, which are different from their bulk counterparts. Due to strong dielectric screening, local heterogeneities such as edges, grain boundaries, defects, strain, doping, chemical bonding, and molecular orientation dictate their physical properties to a great extent. Therefore, there is a growing demand of probing such heterogeneities and their effects on the physical properties of 2D semiconductors on site in a label-free and non-destructive way. Tip-enhanced Raman spectroscopy (TERS), which combines the merits of both scanning probe microscopy and Raman spectroscopy, has experienced tremendous progress since its introduction in the early 2000s and is capable of local spectroscopic investigation with (sub-) nanometer spatial resolution. Introducing this technique to 2D semiconductors not only enables us to understand the effects of local heterogeneities, it can also provide new insights opening the door for novel quantum mechanical applications. This book chapter sheds light on the recent progress of local spectroscopic investigation and chemical imaging of 2D semiconductors using TERS. It also provides a basic discussion of Raman selection rules of 2D semiconductors important to understand TERS results. Finally, a brief outlook regarding the potential of TERS in the field of 2D semiconductors is provided.