The stability of Rivaroxaban (RIVA) drug was determined under different stress conditions in accordance with International Conference on Harmonization (ICH) guidelines Q1A (R2). The chromatogram was developed on precoated silica gel 60F254 TLC plates using ethyl acetate: acetonitrile (5:5 v/v) as a mobile phase. There was no chromatographic interference from the tablet excipients and compact spots were observed for RIVA (Rf = 0.28 ± 0.05). When studied under varied stress conditions, the drug was found susceptible for degradation under acidic and oxide stress conditions. However, it was stable under neutral, thermal and photolytic stress conditions. In total, two degradation products (DPs) were formed. IR and MS/TOF with NMR studies were conducted on a mixture of stressed samples to obtain functional group and mass spectral data. The study data from precise mass study was initially used to pattern a complete mass fragmentation pathway of the drug and later for its degradation products. Considering the best possible molecular formula, structures were suggested for each fragment. Two novel degradation products namely, (R-4-(4-(5-(Aminomethyl)-2-Oxooxazolidin-3-yl) phenyl-Morpholin-3-One HCl and (R-4-(4-(5-(dioxymethyl)-2-Oxooxazolidin-3-yl) phenyl-Morpholin-3-One were identified.