Competitive ability of cereals against segetal weeds depends among other things, on soil properties and the weather. Concerning cornflower (Centaurea cyanus L.), this issue is poorly recognized, as there are no reports on the impact of environmental conditions on the competitiveness of wheat against susceptible and resistant biotypes. Our study aimed to evaluate the effects of site and weather conditions on the competitive effects between winter wheat (WW) and two cornflower biotypes, either florasulam and tribenuron-methyl resistant (R) or sensitive (S). The experiment was conducted in a replacement series model at six sites across Poland in three growing seasons. The competitive relations were determined on the basis of two indices, i.e., the relative biomass and the number of seeds produced by the tested plants. The relative yield of wheat and weed were plotted on graphs and fitted to one of five competition models. In addition, a competitive ratio (CR) was calculated on the basis of fresh plant biomass and the number of seeds. Correlation coefficients were determined between the length of the plant, yield, biomass, the number of seeds per plant, hydrothermal coefficient K, and soil texture. Biometric parameters of wheat for its competition with two cornflower biotypes were analyzed using canonical variate analysis (CVA). The number of days to WW emergence and the day-difference between WW and cornflower (B) emergence were also calculated. The environmental characteristics of the sites, i.e., hydrothermal coefficient K and soil texture, were used as categorizing variables. Drought generally favored the greater competitive ability of WW against B for both biomass accumulation and seed production. During the first season of the research (relatively dry), only in one case out of 12 cases cornflower was more competitive than wheat. In the second year of the experiment (dry season), the competition of WW against B for resources was lower. It depended more on the site than on the cornflower biotype or the proportion of plants in the mixture. Under high or optimal rainfalls (the third year of the experiment), the competitiveness of WW toward B was significantly lower than in years with rainfall deficiency. In addition, the ability of wheat competition against the weed may have been influenced by the earlier emergence of wheat than cornflower. Even though it was sown together with wheat, cornflower emerged 0–12 days later than the tested cereal. It was also noticed that wheat was more competitive on light soils against the herbicide-susceptible (S) biotype. In contrast, greater WW competitiveness was observed against herbicide-resistant (R) cornflower on heavy soils. In conclusion, winter wheat competitiveness against herbicide-resistant or herbicide-sensitive cornflower biotypes is significantly dependent on weather and soil conditions. It is therefore reasonable to study this phenomenon in more detail. It would also be interesting to learn more about the underground competition on varying soil types under different water availability.