Climate change is an important concern worldwide. This huge change is causing a negative impact on crop productivity throughout the whole world and shows some drastic effects on sensitive crops including sweet pepper and other kinds of chilies. These stresses have a negative effect on vegetable growth, fruit quality, and fruit yield. Besides these stresses, accurate planting time is the utmost factor in increasing the crop potential and its productivity. Therefore, this study aimed to evaluate the optimal planting date and best-performing cultivar for sweet pepper to maximize crop productivity, growth, yield, and fruit shelf life under the impacts of climate change. The experiment was conducted in Multan, Pakistan (30° 25 N and 71° 30 E). In this experiment, four planting dates (10 January, 25 January, 10 February, and 25 February) with three cultivars (Ganga, Winner, and Savio) were grown with three replications (each year) during 2020 and 2021. Our findings showed that plant growth, fresh and dry biomass, yield, and yield attributes were statistically higher in earlier plantings, and lower in delayed planting. Regarding the cultivars in both years, ‘Winner’ performed better in all growth and yield parameters as compared to other growing cultivars. Lower weight loss and decay incidence were reported in ‘Winner’ cultivar. Additionally, ‘Winner’ cultivar showed a higher sensory score as compared to the other cultivar in both years. From the results, we conclude that the nursery of sweet pepper plants should be planted on the 25 January to attain higher crop productivity, and the cultivar ‘Winner’ showed promising effects so it should be planted for better yield.