We studied the correspondence between historical series of tree-ring width (TRW) and the normalized difference vegetation index (NDVI, i.e., greenness index) values acquired monthly over an entire year by unmanned aerial vehicles. Dendrochronological techniques revealed differentiated responses between species and seasonality. Pinus engelmannii Carrière and Juniperus deppeana Steudel were affected by warm temperatures (TMAX) during the winter prior to growth and benefited from precipitation (PP) during the seasons prior to the spring period. The standardized precipitation–evapotranspiration index (SPEI) confirmed the high sensitivity of P. engelmannii to drought (r = 0.7 SPEI). Quercus grisea Liebm. presented a positive association with PP at the beginning and end of its growth season. Monthly NDVI data at the individual tree level in the three species (NDVI ~0.37–0.48) statistically confirmed the temporal differences. Q. grisea showed a drastic decrease during the dry season (NDVI = 0.1) that had no impact on drought sensitivity in the same period, according to the climate-TRW relationship. We conclude that a relationship is plausible between the crown greenness index and radial growth, although more extended temporal windows of the NDVI should be explored. Differences in susceptibility to drought found among the species would presumably have implications for the composition of these forests under drought scenarios.