Three protracted droughts have occurred during the instrumental history of Southeast Australia (SEA) – the “Federation” (∼1895–1902), “World War II” (∼1937–1945) and the “Big Dry” (∼1997–present). This paper compares the nature and causes of these droughts in order to better inform drought management strategies in SEA. It is shown that the three droughts differ in terms of severity, spatial footprint, seasonality and seasonal rainfall make-up. This diversity arises due to the fact that the droughts are driven by different climatic teleconnections with the Pacific, Indian and Southern Oceans. Importantly, this study highlights potential flaws with drought forecasting and management in SEA and emphasises the need for further research into understanding and representing hydroclimatic drivers of drought.