The earlier over crops (CCs) are planted, the higher the probability of greater biomass accumulation in the fall, owing to a greater growing degree day accumulation. This is also true for CC termination timing, where later termination in the spring could allow more time for CC growth in the spring. However, the CC growing season’s duration is expected to affect several aspects of the cropping system, such as soil water content, soil fertility, weed demographics, and subsequent crop yield. This experiment’s objective was to evaluate the impact of CC planting and termination timing on CC biomass accumulation, soil water content, crop residue, soil microbial activity, and soil nutrient content, weed demographics, maize grain yield, and yield components during the early stage of CC adoption.