Weed coexistence with an agricultural crop can negatively affect its growth, development, and yield. From this perspective, this study aimed to evaluate weed management strategies and their effect on the agronomic parameters of cowpea cultivation in direct (SPD) and conventional (SPC) planting systems. The experiment was set up in a completely randomized block design with a split-plot arrangement with four replications. The plots received a source of variation referring to the planting systems (direct and conventional planting), and the subplots corresponded to ten weed management strategies (manual hoeing 18 days after planting (DAP); at 36 DAP; at 54 DAP; at 18 and 36 DAP; at 18 and 54 DAP; at 18 and 72 DAP; at 36 and 54 DAP; at 36–72 DAP; at 18, 36, and 54 DAP; and a control with no hoeing). Density and dry mass evaluations of the cowpea plants were performed at harvest (72 DAP) by determining the number of pods per plant, pod length, number of grains per pod, 1000-grain mass, and yield. A total of 28 species distributed in 12 botanical families were identified in the two cultivation systems. The family Poaceae showed the highest frequency, with 25% of the species identified. At the end of the assay, treatment 20 had the highest positive influence and provided significant quantitative gains to the complex of traits related to cowpea production (SPD and hoeing at 18, 36, and 54 DAP). UPGMA cluster analysis and canonical discriminant analysis were performed and allowed a better classification of the evaluated treatments. It was observed that the first two canonical variables explained 90.8% of the total variance contained in the original variables. The use of SPD with weeding at 18, 36, and 54 days after planting provides greater weed control and significant quantitative gains for the complex of characteristics related to cowpea production. The results underscore the importance of choosing the correct cropping system and implementing effective weeding practices to optimize weed control and improve crop performance.