The adoption of dicamba-resistant cotton (Gossypium hirsutum L.) cultivars allows using dicamba to reduce weed populations across growing seasons. However, the overuse of this tool risks selecting new herbicide resistant biotypes. The objectives of this research were to determine the population trajectories of several weed species and track the frequency of glyphosate-resistant Palmer amaranth (Amaranthus palmeri S. Watson) (GR) over 8 years in dicamba-resistant cotton. An experiment was established in North Carolina in 2011, and during the first four years, different herbicide programs were applied. These programs included postemergence applications of glyphosate, alone or with dicamba, with or without residual herbicides. During the last 4 years, all programs received glyphosate plus dicamba. Biennial rotations of postemergence applications of glyphosate only and glyphosate plus dicamba postemergence with and without preemergence herbicides were also included. Sequential applications of glyphosate plus dicamba were applied to the entire test area for the final 4 years of the study. No herbicide program was entirely successful in controlling the weed community. Weed population trajectories were different according to species and herbicide program, creating all possible outcomes; some increased, other decreased, and others remained stable. Density of resistant A. palmeri increased during the first 4 years with glyphosate only programs (up to 11739 plants per m2) and decreased a 96% during the final 4 years when glyphosate plus dicamba was implemented. This species had a strong influence on population levels of other weed species in the community. Goosegras [Eleusine indica (L.) Gaertn.] was not affected by A. palmeri population levels and even increased its density in some herbicide programs, indicating that not only herbicide resistance but also reproductive rates and competitive dynamics are critical for determining weed population trajectories under intensive herbicide-based control programs. Frequency of GR reached a maximum of 62% after 4 years and maintained those levels until the end of the experiment.