Efficient crop management strategies and optimized agricultural practices are pivotal in maximizing overall yield of crops. An essential aspect of improving crop yield is tracking the phenological development of crops, which plays a crucial role in carrying out timely crop management activities, including irrigation, fertilization, pest control, and harvest. However, the lack of resources to acquire data for phenological detection in under-developed countries and the influence of climatic factors on phenology, pose significant challenges. Our work proposes a cost-effective methodology that harnesses the power of Earth Observation (EO) data to acquire essential ground data without the need to rely on manual collection. With a focus on South Asia region, we delve into the analysis of EO data for monitoring wheat phenology and its dynamic interactions with climatic factors. The study focuses on five wheat phenological stages (stem elongation, heading, medium milk, hard dough, and harvest) from 2020 to 2022. Breakpoint and extrema analysis following curve-fitting of Normalized Differential Vegetation Index (NDVI) from Sentinel-2 data accurately detects heading, medium milk, hard dough, and harvest with a one-to-three-day average difference for both years. Stem elongation is detected with a seven-day difference in 2021 and 2022. Furthermore, our analysis reveals that a significant temperature surge in 2022, coupled with minimal precipitation, causes an earlier maturation of the crop compared to in 2021. We thoroughly investigate this effect for 2021 and 2022 to assess the impact of the rate of change in weather conditions on wheat phenology. Embracing these findings can foster sustainable and productive agricultural practices.