Purpose Although low-molecular-weight heparin (LMWH) remains the standard of care, factor Xa inhibitors such as rivaroxaban may serve as an alternative treatment for venous thromboembolism (VTE) in patients with active malignancy. The purpose of the analysis was to evaluate outcomes of VTE management in cancer patients treated with rivaroxaban compared to enoxaparin. Methods This single-center retrospective analysis was conducted on patients with malignancy-associated VTE initiated on treatment with either rivaroxaban or enoxaparin. The primary endpoint was the incidence of recurrent VTE. Secondary outcomes included a comparison in rates of bleeding, mean duration of treatment, and mean time to recurrence of VTE. Results A total of 45 patients were included in each group. The incidence of recurrent VTE was 8.9% in the rivaroxaban group versus 13.3% in the enoxaparin group ( p = 0.53). There were no statistically significant differences in the secondary outcomes with the exception of longer mean duration of treatment in the rivaroxaban group compared to the enoxaparin group (169 vs. 110 days, respectively; p = 0.04). Conclusions This study provides important preliminary information regarding the efficacy and safety of rivaroxaban for treatment of VTE in cancer patients. Although LMWH should remain the standard of care, these results provide initial reassurance that rivaroxaban serves as a viable alternative in the event that injectable anticoagulation is not an acceptable approach to VTE management.