Living mulches can provide many sustainability benefits. However, living mulch–cash crop competition and unreliable weed control are major challenges in living mulch systems. In this study, we evaluated the potential of herbicides used at reduced rates in combination with living mulch to suppress weeds, while simultaneously reducing living mulch vigor. Herbicide treatments were a combination of two POST applications, each consisting of a single, different herbicide. Field trials were conducted in Freeville, NY, USA, using: fresh market field tomato as cash crop; sesbania and sunn hemp as living mulch; and the herbicides fomesafen, halosulfuron, metribuzin, and rimsulfuron. In 2015, when water was not limiting, tomato yield and living mulch biomass were positively correlated. This relationship was negative in 2016, likely because of drought during the growing season. Compared with the untreated living mulch check, using the herbicide treatments in combination with living mulch reduced tomato yield losses by up to 71% in 2015 and 51% in 2016. In these herbicide plus living mulch plots, weed biomass was reduced by up to 97%, compared with the weedy check. Living mulch in herbicide treatments generated up to 2500 kg ha−1 of dry matter during both 2015 and 2016, with an average ground cover of 63% in 2015 and 85% in 2016. A predominantly PRE herbicide with residual soil activity (metribuzin), followed by a herbicide with greater POST activity (halosulfuron/rimsulfuron) was the most effective herbicide application sequence. Results from our study indicate that well-designed herbicide applications may enhance the practicability of living mulch systems.