The purpose of this work was to evaluate the potential of Singular Spectrum Analysis (SSA) and the Fisher–Shannon method to analyse NDVI MODIS time series and to capture and estimate inner vegetation anomalies in forest covers. In particular, the Fisher–Shannon method allows to calculate two quantities, the Fisher Information Measure (FIM) and the Shannon entropy power (SEP), which are used to characterise the complexity of a time series in terms of organisation/disorder. Pilot sites located both in urban (Milano, Torino, and Roma) and peri-urban areas (Appia Park, Castel Porziano, and Castel Volturno) were selected. Among the six sites, Roma, Castel Porziano, and Castel Volturno are affected by the parasite Toumeyella parvicornis. The time series was analysed using the products available in Google Earth Engine. To explore and characterise long-term vegetation dynamics, the time series was analysed using a multistep processing chain based on the (i) normalisation of the satellite time series, (ii) removal of seasonality and any other periodical cycles using SSA, (iii) analysis of the de-trended data using the Fisher–Shannon statistical method, and (iv) validation through comparison with independent data and ancillary information. Our findings point out to a clear discrimination between healthy and unhealthy sites, being the first (Milano, Torino, Appia) characterised by a larger FIM (lower SEP) and the second (Roma, Castel Porziano, Castel Volturno) by a lower FIM (larger SEP). The results of the investigations showed that the use of the SSA and Fisher–Shannon statistical methods coupled with the NDVI time series of the MODIS satellite made it possible to effectively identify and characterise subtle but physically significant signals veiled by seasonality and annual cycles.