In this work we report the results of RS measurements on some common military explosives and some of the most common explosives precursors deposited on clothing fabrics, both synthetic and natural, such as polyester, leather and denim cotton at concentration comparable to those obtained from a single fingerprint. RS Spectra were obtained using an integrated portable Raman system equipped with an optical microscope, focusing the light of a solid state GaAlAs laser emitting at 785 nm. A maximum exposure time of 10 s was used, focusing the beam in a 45 μm diameter spot on the sample. The substances were deposited starting from commercial solutions with a Micropipetting Nano-Plotter, ideal for generating high-quality spots by non-contact dispensing of sub-nanoliter volumes of liquids, in order to simulate a homogeneous stain on the fabric surface. Images acquired with a Confocal Laser Scanning Microscope provided further details of the deposition process showing single particles of micrometric volume trapped or deposited on the underlying tissues. The spectral features of each substance was clearly identified and discriminated from those belonging to the substrate fabric or from the surrounding fluorescence. Our results show that the application of RS using a microscope-based apparatus can provide interpretable Raman spectra in a fast, in-situ analysis, directly from explosive particles of some μm3 as the ones that it could be found in a single fingerprint, despite the contribution of the substrate, leaving the sample completely unaltered for further, more specific and propaedeutic laboratory analysis. The same approach can be envisaged for the detection of other illicit substances like drugs.