The monsoon rainfall variability in semi-arid regions affects all economic activities in general and agricul-ture in particular. The present study, therefore, ana -lyses monsoon rainfall variability and its connection with El Ni??o Southern Oscillation (ENSO), Indian Ocean Dipole (IOD) and agriculture in the semi-arid region of Maharashtra, India during 1980???2014. Li-near correlation and regression analysis were carried out to evaluate the role of ENSO and IOD in rainfall variability. The standardized precipitation index (SPI), standardized cropped productivity index (SCPI) and standardized crop area index (SCAI) were used to compare the agro-meteorological variability. The de-pendency of agricultural cropped area on rainfall was verified using satellite data (NDVI). The El Ni??o events and positive phase of IOD were mainly respon-sible for below-average rainfall over the study region. This highlights the need to incorporate the ENSO and IOD for precise forecasting of monsoon rainfall. Rain-fall variability (up to 33%) over the study basins caus-es meteorological droughts and eventually results in agricultural droughts. The agricultural productivity of rainfed as well as irrigated crops was significantly affected by rainfall variability. Particularly, during the severe meteorological droughts (1985???86, 2002???03 and 2012), agricultural productivity and cropped area were significantly reduced. Under the future climate change scenario, a rise in temperature will further add to the already difficult agricultural water man-agement challenge. Therefore, agronomists and water resources managers have to design a judicial plan which can mitigate the water scarcity and sustain agricultural yield even in warming conditions.