Extreme climatic events pose significant challenges to natural resource management and jeopardize the sustainability of rainfed agriculture. This research investigates the interactions between Climate Extreme Indices (CEIs) and Weather-Related Crop Production Indicators (WRCPIs) for wheat (Triticum aestivum) and olives (Olea europaea) within Jordan's diverse agroecological zones utilizing stepwise multiple regression analysis. We also examined correlations and trends spanning from 1995 to 2022 across four key regions: Irbid, Amman, Mafraq, and Karak. Findings reveal that precipitation-related indices based on a station in Irbid exhibit a positive correlation with Jordan's wheat yield (correlation coefficient > + 0.41), suggesting the beneficial effects of increased moisture variability. Conversely, temperature indices based on Karak station demonstrate a stronger correlation with wheat production (correlation coefficient > - 0.45). For olive cultivation, CEIs such as the Average Temperature of Cold Months and the Optimum Temperature (OPT) are positively correlated with production outcomes (correlation coefficients ranging from 0.43 to 0.55). In contrast, production faces negative correlations (-0.41 to -0.56) with indices like Diurnal Temperature Range (DTR), Frost Days, and Maximum Daily Maximum Temperature. Zone-specific regression models significantly enhance predictive accuracy, reflecting the nuanced influence of CEIs and WRCPIs. In Irbid, olive production is notably influenced by factors including Consecutive Dry Days, the Simple Day Intensity Index (SDII), and Maximum Minimum Temperature. In Amman and Mafraq, optimal models highlight temperature variables, including OPT, Minimum Temperature, Spring Average Highest Temperature, and Annual Average Temperature (AAT) as critical predictors. Trend analyses suggest potential increases in wheat yields in Irbid and Karak, attributed to rising DTR and a declining frequency of Growing Season Minimum Temperatures below 5 degrees C. Olive production is also projected to rise, driven by upward trends in OPT, SDII, and AAT. These results underscore the vulnerability of rainfed agriculture to climatic extremes and emphasize the urgent need for proactive adaptation strategies. Policymakers are urged to implement targeted management practices to bolster resilience and ensure the sustainability of agricultural productivity in the face of climate variability.