As a result of intensive herbicide protection of crops against silky bentgrass (Apera spica-venti (L.) P. Beauv), numerous herbicide-resistant biotypes have been selected, mainly from the group of acetolactate synthase (ALS) inhibitors. We analyzed the development of herbicide-sensitive and herbicide-resistant biotypes of bentgrass and winter wheat under competition, taking into account selected physical and chemical properties of the soil, including nitrogen fertilization. The pot experiment (additive model) was conducted in the 2018/19 and 2019/20 seasons. The experimental factors included: (1) bentgrass with different sensitivity levels to herbicides from the groups HRAC/WSSA 1 and HRAC/WSSA 2, specifically two sensitive and three resistant biotypes; (2) two types of soil, sandy and clay; and (3) nitrogen fertilization, both with and without fertilization. Winter wheat and bentgrass development was assessed during each growing season, every 5 or 3 days from September until May, using the BBCH scale. The emergence date of the tested species/biotypes was recorded. The development of competing species was compared based on a new, proposed index: the duration of the developmental phases. As a result, the soil type and fertilization level differentiated wheat and bentgrass emergence dates and development. The autumn development of the competing species was slower and more uniform than the spring one. At the same time, the dynamics of the bentgrass and wheat development in the spring were greater. Bentgrass and winter wheat emerged earlier and grew more intensively on clay and fertilized soil. To sum up, no clear relationship was found between the resistance/sensitivity of bentgrass to herbicides and changes in the phenological development of plants in competition with winter wheat.