This study utilised multi-temporal satellite data to characterize droughts across the five Agro-ecological zones (AEZ) of Zimbabwe at monthly, seasonal, sub-seasonal and annual scales (2000 to 2018) using a combination of Satellite Pour l'Observation de la Terre (SPOT) Vegetation (VGT) and Project for On-Board Autonomy-Vegetation (PROBA-V) derived Vegetation Condition Index (VCI). The characterized droughts were validated, using maize yield and meteorological station derived Standardised Precipitation Index (SPI). The study showed differential spatial and temporal expression of drought in Zimbabwe, over the 19-year study period. November had the highest frequency of drought while the first quarter of the season experienced more droughts than the second quarter. Spatially, virtually all AEZ in Zimbabwe are prone to droughts and the frequency is increasingly, with the Agro-ecological region five (southern Zimbabwe) being the worst affected. Further, the study found a strong positive relationship between the VCI and maize yield (r = 0.701, P = 0.000), demonstrating the utility of the index in drought monitoring at national level. Overall, findings from this work highlight the significance of using multi-date and national-scale analysis of agricultural drought occurrence and trends. Moreover, this work provides critical baseline information for developing drought resilience and mitigation strategies in drought-prone areas.