Drought-induced forest dieback can lead to a tipping point in community dominance, but the coupled response at the tree and stand-level response has not been properly addressed. New spatially and temporally integrated monitoring approaches that target different biological organization levels are needed. Here, we compared the temporal responses of dendrochronological and spectral indices from 1984 to 2020 at both tree and stand levels, respectively, of a drought-prone Mediterranean Pinus pinea forest currently suffering strong dieback. We test the influence of climate on temporal patterns of tree radial growth, greenness and wetness spectral indices; and we address the influence of major drought episodes on resilience metrics. Tree-ring data and spectral indices followed different spatio-temporal patterns over the study period (1984–2020). Combined information from tree growth and spectral trajectories suggests that a reduction in tree density during the mid-1990s could have promoted tree growth and reduced dieback risk. Additionally, over the last decade, extreme and recurrent droughts have resulted in crown defoliation greater than 40% in most plots since 2019. We found that tree growth and the greenness spectral index were positively related to annual precipitation, while the wetness index was positively related to mean annual temperature. The response to drought, however, was stronger for tree growth than for spectral indices. Our study demonstrates the value of long-term retrospective multiscale analyses including tree and stand-level scales to disentangle mechanisms triggering and driving forest dieback.