Canola (Brassica napus L.) is an important oilseed crop that provides essential vegetable oil but faces significant competition from weeds that are influenced by various agronomic practices and environmental conditions. This study examines the complex interactions between canola stand density and weed intensity over three growing seasons, identifying a total of 27 weed species. It is important to establish a connection between the density of winter canola stands, the intensity of weeding and the response of individual weed species in real conditions. The case study was executed on plots located in the Přerov district (Olomouc region, Czech Republic). The assessment was carried out during two periods—autumn in October and spring in April. Canola plants (plant density) were counted in each evaluated area, weed species were identified, and the number of plants for each weed species was determined. Half of the plots were covered with foil before herbicide application to prevent these areas from being treated with herbicides. We used redundancy analysis (RDA) to evaluate the relationships between canola density and weed dynamics, both with and without herbicide treatment. The results show the ability of canola to compete with weeds; however, that is factored by the density of the canola stand. In dense stands (over 60 plants/m²), canola is able to suppress Galium aparine L., Geranium pusillum L., Lamium purpureum L., Papaver rhoeas L. and Chamomilla suaveolens (Pursh) Rydb. Nevertheless, there are weed species that grow well even in dense canola stands (Echinochloa crus-galli (L.) P. Beauv., Phragmites australis (Cav.) Steud., Tripleurospermum inodorum (L.) Sch. Bip. and Triticum aestivum L.). These findings highlight the potential for using canola stand density as a strategic component of integrated weed management to reduce herbicide reliance and address the growing challenge of herbicide-resistant weed populations. This research contributes significantly to our understanding of the dynamics of weed competition in canola systems and informs sustainable agricultural practices for improved crop yield and environmental stewardship.