This research presents three case studies of low temperature anomalies that occurred during the winter–spring seasons and their influence on extreme events and crop production. We investigate causes and effects of each climate event and developed prediction methods for crops based on the climate diagnostic information. The first study diagnosed the driven environmental-factors, including climate pattern, climate change, soils moisture, and sea level height, associated with the 2011 great flood in Thailand and resulting total crop loss. The second study investigated climate circulation and indices that contributed to wet-and-cold (WC) events leading to significant crop damage in Taiwan. We developed empirical–dynamical models based on prominent climate indices to confidently predict WC events as much as 6 months before they occur. The final study extends from the second study and predict chronic damage to rice crops from climate change by using a crop simulation model. The long-term prediction of rice growth and yield effectively illustrated both decreases and increases in yield depending on climate scenarios. The three studies are different in location and circumstances but the methodologies can be applied across Thailand, Taiwan, and other areas with similar agroclimatology.