Crop rotations dominated by winter annual crops and relying on the use of herbicides to control weeds have resulted in weed communities dominated by a few highly specialized species such as Alopecurus myosuroides. Integrated weed management (IWM) represents a sensible strategy to target such difficult weeds, through a combination of preventive, cultural, and direct means. In six field trials over three years, we tested the effect of stale seedbed preparation, winter wheat seed rate, and chemical weed control strategy on Alopecurus myosuroides control efficacy and variability in efficacy. The field experiments were carried out under reduced tillage practice and without pre-sowing use of glyphosate. Stale seedbed preparation alone reduced A. myosuroides infestation level by 25% on average. No clear effect was found of increasing winter wheat seed rate from 300 to 400 seeds m−2. A combination of stale seedbed preparation and herbicide treatment in autumn and spring was found to be synergistic, improving weed control efficacy significantly and moreover reducing the variability in control efficacy and hence the risk for weed control failure.