Vegetation cover can regulate regional climate and associated dry–wet variations. However, the effects of the quantitative structure and landscape pattern of vegetation cover on climatic drought remain unclear. Yunnan Province in China, with its abundant vegetation resources, provides a good setting for addressing this research gap. Our objective is to provide guiding recommendations for climate-warming mitigation through the study of the topic. This study adopted four periods of vegetation cover data, from 1992 to 2020, and explored their dynamics. Monthly average precipitation and temperature data from 125 meteorological stations in Yunnan were used to calculate standardized precipitation–evapotranspiration index (SPEI) for 1992–2020 to understand the responses of climatic drought to vegetation cover dynamics. The correlations between quantitative structure, landscape pattern, and climatic drought were investigated by Pearson’s correlation coefficient in 10 km, 20 km, 30 km, and 40 km grid cells, respectively. The results indicate that changes in the quantitative structure of vegetation could influence regional climates, with the contributions to climatic drought mitigation ranked in the following order: broad-leaved forest > shrubland > needle-leaved forest > cropland > grassland. Landscape patterns significantly affected local climates, where broad-leaved and needle-leaved forests had the strongest and most stable correlations with climatic drought, whereas shrubland and grassland showed weaker correlations. The correlations between landscape patterns and climatic drought were stronger during the dry season than the rainy season. Factors such as the landscape dominance index, fragmentation index, and aggregation index had a significant impact on climatic drought. The dominant and aggregated-distribution broad-leaved forests were conducive to climatic drought mitigation, while needle-leaved forests, croplands, and grasslands might exacerbate climatic drought.