Winter wheat (Triticum aestivum L.) is a highly competitive crop with the potential to enhance on-farm revenue and reduce reliance on crop protection inputs. The adoption of winter wheat in the Canadian Prairies has varied significantly over recent decades; however, improved weed and disease management practices could facilitate stability of hectares cultivated. To assess current and alternative pesticide management practices, we conducted a study across 15 site-years at four locations over 4 years (2018–2022). Experimental treatments included pre-plant weed management (glyphosate vs. glyphosate mixed with pyroxasulfone + carfentrazone-ethyl), in-crop weed management (no in-crop herbicide vs. fall-applied 2,4-D vs. fall-applied 2,4-D + spring-applied site-year-specific herbicides), and in-crop fungicide management (no in-crop fungicide vs. one prothioconazole + tebuconazole application at Zadoks Growth Stage (ZGS) 60 vs. two prothioconazole + tebuconazole applications at ZGS32 and ZGS60). Pre-plant glyphosate alone and glyphosate tank-mixed with pyroxasulfone + carfentrazone-ethyl exhibited comparable effects on grain yield, quality parameters, and agronomic characteristics. In-crop weed management had no significant influence on these factors compared to the no in-crop herbicide control, suggesting that in-crop herbicide applications are unnecessary due to the high competitiveness of winter wheat against weeds. However, disease mitigation was prudent as single and double application of fungicide increased grain yield while maintaining grain protein concentration levels. A high-yielding, stable system for optimal grain yield typically required pre-plant weed management coupled with two fungicide applications. These observations confirm herbicide inputs can be reduced in a winter wheat cropping system, but disease pressure requires careful cultivar selection with respect to disease resistance as multiple applications of fungicides were needed to optimize grain yield.