Given the potential impact of improvements to on-site drug testing, as well as recent, successful displays of paper spray ionization mass spectrometry (PSI-MS) in this regard, this thesis pilots the implementation of Raman spectroscopy as a compliment to MS for field-based confirmatory drug testing. Surface enhanced Raman scattering (SERS) is utilized for applications to trace detection. Two-tiered analysis of individual drug samples is enabled using triangularly-cut plasmonic papers, from which both SERS and PS-MS analysis may be performed. Several drug compounds, representative of traditional and emerging drug types, are examined by these techniques, both separately and as a fully integrated, SERS-PSI-MS testing platform. The unique benefits offered by Raman/SERS are demonstrated via discrimination of isomers that are indistinguishable by MS. Optimization of the coupled, analytical platform culminate in a standard operating procedure, which is implemented in an error-rate study (N = 500) performed for sub-microgram quantities of drugs deposited on plasmonic papers