Oak stands are declining in many regions of southern Europe. The goal of this paper is to assess this process and develop an effective monitoring tool for research and management. Long-term trends of the Normalized Difference Vegetation Index (NDVI) were derived and mapped at 30-m spatial resolution for all areas with a stable land cover of cork oak (Quercus suber L.) and holm oak (Quercus ilex L.) forests and agroforestry systems in mainland Portugal. NDVI, a good proxy for forest health and productivity monitoring, was obtained for the 1984–2017 period using Landsat-5 TM and Landsat-7 ETM+ imagery. TM values were adjusted to those of ETM+, after a comparison of site-specific and literature linear equations. The spatiotemporal trend analysis was performed using only July and August NDVI values, in order to minimize the spectral contribution of understory vegetation and its phenological variability, and thus, focus on the tree layer. Signs and significance of trends were obtained for six representative oak stands and the whole country with the Mann Kendall and Contextual Mann-Kendall test, respectively, and their slope was assessed with the Theil-Sen estimator. Long-term forest inventories of six study sites and NDVI time series derived from the Moderate Resolution Imaging Spectroradiometer (MODIS) allowed validating the methodology and results with independent data. NDVI has a good relationship with cork production at the forest stand level. Pettitt tests reveal significant change-points within the trends in the period 1996–2005, when changes in drought patterns occurred. Twelve percent of the area of oak stands in Portugal presents significant decreasing trends, most of them located in mountainous regions with shallow soils. Cork oak agroforestry is the most declining oak forest type, compared to cork oak and holm oak forests. The Google Earth Engine platform proved to be a powerful tool to deal with long-term time series and for the monitoring of forests health and productivity.