The recent spells of recurrent and consecutive droughts in the Bundelkhand region in Central India have led to uncertain rain-fed agriculture and its sustainability. Adequate knowledge of starting dates and lengths of dry spells has a considerable importance in rain-fed agriculture, irrigation planning, and various decision-making processes. The long dry spells incur heavy costs to the affected communities in the form of lost crop production and reduced crop yield, particularly in semi-arid regions. The sustainability of agriculture very much depends on the provision of supplemental irrigation during droughts, for which a detailed analysis of dry spells is a pre-requisite. An attempt has been made to study the temporal variation of dry spell lengths to identify whether it can be related to climate change. The dry spell analysis revealed that two critical dry spells with spell lengths of 10 days and more occurs invariably every year and therefore rain-fed agriculture needs adequate supplemental irrigation backup for sustainable operations under such a scenario. The supplemental irrigation requirements have been estimated for each critical dry spell period for all development blocks in each district, which will provide useful inputs to decision-makers for planning agricultural operations during an impending drought scenario.