Soil fertility and disturbance can potentially modify weed dynamics in a corn–soybean rotation. Knowing how added mineral fertilizers and tillage influence weed populations in the long term can provide insight into weed community shifts, which may affect future weed management requirements. The first objective of this study was to evaluate the effect of 24 to 25 years of nitrogen and phosphorus fertilization treatments and tillage (moldboard vs. no-till) on weeds (density, biomass, and composition) before and after herbicide applications in 2016/corn and 2017/soybean. The second objective was to evaluate the effect of the same treatments 6 yr after no postemergence weed management in 2022/corn. Since the last evaluation performed in 2004, weed density, richness, and diversity increased, and more annual grasses were observed under both tillage regimes. No fertilization effect was observed on any weed variables, including composition, except for increased biomass when left to grow all season after crop planting. In managed plots, the density and biomass of annuals and perennials were generally higher in no-till, and discrepancies were highest for annual grass densities before herbicide application. Weed species richness and diversity based on counts were equivalent between tillage regimes, but total biomass was distributed between more species in no-till. Higher weed densities and concurrent weed biomass, observed in no-till, reduced crop yields in 2016/soybean only. The combination of low crop diversity and low use of residual herbicides during the trial potentially led to the observed species shifts and increased weed density.