Several colonisation projects were implemented in the Brazilian Legal Amazon in the 1970s and 1980s. Among these colonisation projects, the most prominent were those with the “fishbone” and “topographic” models. Within this scope, the settlements known as Anari and Machadinho stand out because they are contiguous areas with different models and structures of occupation and colonisation. The main objective of this work was to evaluate the dynamics of Land-Use and Land-Cover (LULC) in two different colonisation models, implanted in the State of Rondônia in the 1980s. The fishbone and topographic or Disorganised Multidirectional models were implemented in the Anari and Machadinho settlements, respectively. A 36-year time series of Landsat images (1984–2020) was used to evaluate the rates and trends in the LULC process in the different colonisation models. In the analysed models, a rapid loss of primary and secondary forests (anthropized areas) was observed, mainly due to the dynamics of its use, established by the Agriculture/Pasture relation with a heavy dependence on road construction. Understanding these two forms of occupation can help the future programs and guidelines of the Brazilian Legal Amazon and any tropical rainforest across the globe.