Cover crops have increased in popularity in midwestern U.S. corn and soybean systems in recent years. However, little research has been conducted to evaluate how cover crops and residual herbicides are effectively integrated together for weed control in a soybean production system. Field studies were conducted in 2016 and 2017 to evaluate summer annual weed control and to determine the effect of cover crop biomass on residual herbicide reaching the soil. The herbicide treatments consisted of preplant (PP) applications of glyphosate plus 2,4-D with or without sulfentrazone plus chlorimuron at two different timings, 21 and 7 d prior to soybean planting (DPP). Cover crops evaluated included winter vetch, cereal rye, Italian ryegrass, oat, Austrian winter pea, winter wheat, and a winter vetch plus cereal rye mixture. Herbicide treatments were applied to tilled and nontilled soil without cover crop for comparison. The tillage treatment resulted in low weed biomass at all collection intervals after both application timings, which corresponded to tilled soil having the highest sulfentrazone concentration (171 ng g−1) compared with all cover crop treatments. When applied PP, herbicide treatments applied 21 DPP with sulfentrazone had greater weed (93%) and waterhemp (89%) control than when applied 7 DPP (60% and 69%, respectively). When applied POST, herbicide treatments with a residual herbicide resulted in greater weed and waterhemp control at 7 DPP (83% and 77%, respectively) than at 21 DPP (74% and 61%, respectively). Herbicide programs that included a residual herbicide had the highest soybean yields (≥3,403 kg ha−1). Results from this study indicate that residual herbicides can be effectively integrated either PP or POST in conjunction with cover crop termination applications, but termination timing and biomass accumulation will affect the amount of sulfentrazone reaching the soil.