<p>Increasing crop production is essential to ensure food security for the growing population. To enhance yield, it is necessary to identify the yield gap and the contributing factors in crop production in each region. For this purpose, the production of wheat, barley, and canola—three major crops under winter cropping system in Kurdistan province, west of Iran—was documented, and the yield gap was determined using boundary line analysis (BLA). The documentation results indicated that in 50% of wheat, barley, and canola farms, the seed consumption varied significantly. Additionally, 50% of farmers applied more than 50 kg/ha of fertilizers. The average plant density was 422 plants/m² for wheat, 340 plants/m² for barley, and 54 plants/m² for canola. Farmers’ experience varied widely. Based on the BLA results, the following recommendations were made to increase yields and address yield gaps: (1) Apply specific amounts of nitrogen and phosphorus fertilizers. (2) Use minimum seed rates for each crop. (3) Maintain appropriate plant densities. (4) Irrigate at optimal intervals depending on rainfall and air dryness. Overall, by optimizing the management of key agricultural factors such as fertilizer application, seed rate, and plant density, there is significant potential to improve crop yields in the studied region.</p>